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... h; b Conversion determined by 1H NMR; c5 mol% PPh3 Table 1 - Tertiary Amine... h; b Conversion determined by 1H NMR; c5 mol% PPh3 Table 2 - Secondary Amine....4 MHz, CDCl3, 25 °C): δ = 145.9 (C6), 142.3 (C10), 128.5 (C12), 128.5 (C8... (75.4 MHz, CDCl3, 25 °C): δ = 144.4 (C5), 142.4 (C9), 118 Chapter 7 128.6 (C7....4 MHz, CDCl3, 25 °C): δ = 146.4 (C9), 142.5 (C5), 128.8 (C11), 128.4 (C6 & C7... NMR (75.4 MHz, CDCl3, 25 °C): δ = 142.3 (C5), 140.5 (C9), 128.5 (C7 & C11... C NMR (75.4 MHz, CDCl3, 25 °C): δ = 142.7 (C5), 140.1 (C9), 129.0 (C10), 128... NMR (75.4 MHz, CDCl3, 25 °C): δ = 142.6 (C5), 128.5 (C7), 127.1 (C6), 125....4 MHz, CDCl3, 25 °C): δ = 142.2 (C4), 128.5 (C6), 128.4 (C5), 125.9 (C7), 50... NMR (75.4 MHz, CDCl3, 25 °C): δ = 142.5 (C9), 128.5 (C11), 128.4 (C10..., 25 °C): δ = 152.2 (C11), 142.8 (C4), 141.9 (C8), 128.5 (C5 & C6), 126.0 (C7... (75.4 MHz, CDCl3, 25 °C): δ = 167.9 (C5), 133.3 (C1), 129.9 (C4), 129... C NMR: (CDCl3, 75.4 MHz) δ = 168.8 (C5), 134.2 (C1), 131.7 (C4), 128... °C): δ = 140.9 (C4), 128.4 (C6), 128.2 (C5), 125.9 (C7), 38.2 (C1), 31....4 MHz, DMSO-d6, 25 °C): δ = 145.8 (C5), 128.5 (C7), 126.8 (C6), 126... °C): δ = 143.9 (C4), 128.5 (C6), 127.4 (C5), 126.3 (C7), 47.2 (C3), 37... °C): δ = 157.6 (C7), 132.7 (C4), 129.2 (C5), 113.8 (C6), 55.0 (C8), 38... (75.4 MHz, DMSO-d6, 25 °C): δ = 142.1 (C10), 128.2 (C8), 128.2 (C9... (75.4 MHz, CDCl3, 25 °C): δ = 145.7 (C5), 137.7 (C9), 133.7 (C11), 132...), 137.6 (d, J = 9.3 Hz, C1), 124.5 (d, J = 3.0 Hz, C5), 117.3 (d, J = 7.2 Hz, C4), 116.2 (d, J = 21...) δ = 149.6 (C1), 131.8 (C3), 128.9 (C5), 126.4 (C2), 120.4 (C4), 115...) δ = 148.1 (C1), 138.7 (C3), 128.9 (C5), 116.3 (C4), 112.3 (C2), 108...) δ = 148.8 (C1), 134.9 (C3), 129.9 (C5), 115.1 (C4), 111.4 (C2), 109...), 131.5 (d, J = 31.4 Hz, C3), 129.6 (C5), 124.8 (d, J = 272.1 Hz, C9), 114... consistent with literature data.31 142 Chapter 7 4-(3-Phenylpropyl)morpholine 4.15 According...: (CDCl3, 75.4 MHz) δ = 142.2 (C4), 128.5 (C6), 128.4 (C5), 125.9 (C7), 67...); 13C NMR: (CDCl3, 75.4 MHz) δ = 142.5 (C5), 128.4 (C7), 127.5 (C8), 126...); 13C NMR: (CDCl3, 75.4 MHz) δ = 142.6 (C6), 128.4 (C8), 127.5 (C9...: (CDCl3, 75.4 MHz) δ = 142.5 (C3), 128.4 13 (C5), 127.5 (C6), 126.0 (C4...); C NMR: (CDCl3, 75.4 MHz) δ = 13 142.0 (C5), 128.5 (C7), 127.7 (C8), 126...: (CDCl3, 75.4 MHz) δ = 13 142.3 (C9), 138.2 (C5), 129.2 (C11), 128.5 (C6..., 75.4 MHz) δ = 145.7 (C9), 140.2 (C5), 128.8 (C12), 128.5 (C7), 128...) and isolated as a yellow oil (142 mg, 80%). 1H NMR: (CDCl3...) δ = 167.6 (C1), 135.0 (C2), 131.4 (C5), 128.6 (C4), 127.0 (C3), 40..., 75.4 MHz) δ = 163.1 (d, J = 245.4 Hz, C5), 148.7 (d, J = 6.6 Hz, C3), 130.1 (d, J = 8.1 Hz...: (CDCl3, 75.4 MHz) δ = 143.5 (C6), 142.9 (C5), 139.5 (C3), 118.6 (C8), 117....4 MHz) δ = 162.1 (d, J = 244.7 Hz, C6), 142.4 (d, J = 7.1 Hz, C4), 139.1 (d, J = 3.0 Hz, C3....0 (d, J = 8.4 Hz, C8), 115.8 (d, J = 23.0 Hz, C5), 113.1 (d, J = 20.9 Hz, C7), 65....2 (C4), 143.8 (d, J = 1.1 Hz, C3), 130.0 (C5), 128.8 (d, J = 32.3 Hz, C7), 124..., 75.4 MHz) δ = 161.2 (d, J = 243.6 Hz, C5), 145.8 (d, J = 3.8 Hz, C3), 127.4 (d, J = 15...); 13 C NMR: (CDCl3, 75.4 MHz) δ = 142.6 (C5), 141.0 (C6), 136.6 (C3), 129...) δ = 140.0 (C3), 134.6 (C4), 133.4 (C5), 131.9 (C10), 128.8 (C9), 127...); 13C NMR: (CDCl3, 75.4 MHz) δ = 142.6 (C7), 139.1 (C8), 129.1 (C10...) δ = 170 Chapter 7 143.3 (C3), 136.1 (C5), 136.0 (C8), 129.6 (C7), 128....4 (C8), 140.9 & 140.7 (C3), 135.5 (C5), 128.1 & 128.1 (C4), 126.1 & 125...) δ = 208.2 (C1), 142.1 (C3), 138.0 (C4), 128.8 (C6), 126.9 (C5), 46.7 (C8....4 MHz) δ = 208.4 (C2), 142.4 (C3), 138.1 (C9), 132.2 (C5), 128.7 172 Chapter...) δ = 202.2 (C1), 142.2 (C11), 139.0 (C3), 138.0 (C8), 135.6 (C5), 132.3 (C6....4 (C1), 176 Chapter 7 142.9 (C3), 137.5 (C8), 135.0 (C5), 132.3 (C6), 130...), 138.4 (d, J = 3.1 Hz, C4), 128.2 (d, J = 8.1 Hz, C5), 115.5 (d, J = 21.4 Hz, C6), 115..., C8), 146.9 (C2), 137.8 (d, J = 3.1 Hz, C5), 128.3 (d, J = 8.1 Hz, C7), 115.3 (d, J = 21...), 70.1 (C1), 17.4 (C4), 13.4 (C5); Minor 162.2 (d, J = 244.6 Hz, C9....2 (d, J = 8.1 Hz, C9), 128.1 (C2), 126.8 (C5), 115.6 (d, J = 21.4 Hz, C10), 74....3 (d, J = 245.0 Hz, C8), 139.7 (d, J = 3.1 Hz, C5), 134.3 (C3), 127.6 (d, J = 8.1 Hz, C6..., H7), 139.4 (C2), 138.0 (d, J = 7.8 Hz, C5), 136.3 (d, J = 3.1 Hz, C4), 127.8 (d, J = 8.5 Hz...), 138.1 (d, J = 3.5 Hz, C4), 129.6 (d, J = 5.3 Hz, C5), 125.4 (d, J = 8.1 Hz, C9), 125.1 (d, J = 17....7 (C2), 139.6 (d, J = 3.8 Hz, C4), 128.7 (C5), 126.2 (d, J = 7.2 Hz, C9), 121.1 (d, J = 17...), 116.2 (C3), 115.4 (d, J = 17.8 Hz, C5), 74.3 (d, J = 1.3 Hz, C1); 19F NMR...), 125.2 (qd, J = 4.6 1.7 Hz, C9), 124.5 (C5), 122.7 (q, J = 272.0 Hz, C10), 118...), 129.4 (d, J = 8.3 Hz, C7), 127.8 (d, J = 4.2 Hz, C5), 124.5 (d, J = 3.5 Hz, C6), 115.6 (d, J = 21...) δ = 199.2 (C1), 151.0 (C7), 130.4 (C5), 124.6 (C4), 110.8 (C6), 47...) δ = 199.3 (C1), 154.5 (C7), 130.2 (C5), 126.5 (C4), 113.5 (C6), 48...) δ = 199.1 (C1), 152.3 (C7), 130.6 (C5), 124.5 (C4), 110.2 (C6), 49...) δ = 202.1 (C1), 152.9 (C7), 141.7 (C5), 131.7 (C9), 127.8 (C4), 117....5 (d, J = 3.2 Hz, C8), 116.0 (d, J = 21.9 Hz, C5), 66.9 (C11), 50.3 (d, J = 4.4 Hz, C10....6 (C9), 132.5 (C4), 128.2 (q, J = 5.4 Hz, C5), 125.8 (d, J = 29.6 Hz, C6), 123...



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...-1,3-пентадиена с заданными молекулярными характеристиками» C1-142 C. А. Романов, С. Ю. Ердяков, М. Е. Гурский, Е.С.Гарина, М.Ю. Заремский... и их молекулярных масс турбореометрическим методом» C5-142 Д.А. Маркелов, Ю.Я. Готлиб «Зависимость механических свойств..., C. Plesse, D. Teyssié, C. Chevrot, Synthetic Metals, 142, (2004 )287. 3. F. Vidal, C. Plesse, G. Palaprat... Президиума РАН "Поддержка инноваций и разработок". 142 Секция 2 Устные доклады Акриловые сополимеры..., С5204 Алешин В.В. C3-3 Алиев Л.П. C5-8 Алиев М.А. C5-3, C5-4 Алиновская В.А. C1-197, C2-57..., 276, C4-79, C5-7, C5-81, C5205,C5-207, C5-268 Бакеева И.В. C4-9, C4..., C5-115, C5143 Балабанова Ф.Б. C1-70 Балакин В.М. C1-11, C5187 Балакин К.В. 142 Балакина М.Ю. C3-7, C329, C3-103 Балашов В.А. C1-12, C5-15 Бандурян С.И. C5..., C2-54, C2-55 Бачурин С.О. 142 Баяхметова З.К. C3-77 Беганцова Ю.Е. C3... Бубнов М.П. C1-192 Бубнов Ю.Н. C1-142 Бубнова Л.И. 184 Бугаенко М.Г. 100 Бугаков..., C1177, C4-29, C5-32, C5-33, C5-42, C5-46, C5-166, C5167 Бузинова... Е.В. C5-41 Бурда В.В. C5-27, C5-249 Бурдуковский В.Ф. 108 Бурмистров В.А. C5-22 Бурова Т.В. 254, C5..., C4-79, C5-7, C581, C5-205, C5-207, C5-238, C5-239, C5-268 Вольфсон С.И. C1... О.В. 240 Вялова А.Н. C5-51 Габдрахманов Д.Р. C5-52, C5-53 Габитов И.Т. C1-7, C5-9 Габриелян Г.А. C2... Ганев В. C5-43 Ганина Л.В. C5-56 Ганифаева Н.А. C5-8 Гаппарова Г.И. C1-138, C5-57, C5-58 Гараева Г.Ф. C1-33 Гарина Е.С. C1-76, C1-142, C1-152, C1-195, C5-100 Гарифуллин Д.Ш. C1-11 Гаришин О.К. C5-59..., C5-60 Гегель Н.О. C5-257 Ген Д.Е. 243 Герасименко С.А. C5-61 Герасимов В.И. C5-181, C5-205 Герасимов Р.А. C5-62 Герасин В.А. 190, C1-5, C219, C5-59, C5-63, C5..., C1-76, C1-195, C1-142, C1-143, C1178, C3-17...-96, C1-152, C5-210 Готлиб Ю.Я. 220, C5-74, C5-142 Гофман И.В. 234, C3... В.Я. 254, C5-36, C5-75, C5-84 Гринберг Н.В. 254, C5-36, C5-75, C5-84 Грингольц..., C4-12 Гурский М.Е. C1-142 Гусарова Е.Б. C5-104 Гусев А.В. 244 Гусев К.И. C4..., C2-19, C5-59, C5-63, C5-78 Гуткович С.А. C5-79 Даванков В.А. C5-178 Давиденко... П.В. 246, C580, C5-224 Добровольская И.П. 234, C5-83, C5-191 Добрун Л.А. C5-134 Добрусина... А.В. C4-9 Долгих О.В. C5-158 Долгов В.В. 201 Долгова А.А. C5-7, C5-81 Долгоносова А.М. C5-259 Долгополов...-43 Дубовик А.С. 254, C5-36, C5-75, C5-84 Дубовицкий В.А. C5-48 Дубровский В.В. C4..., C1187, C3-49, C5-107 Ердяков С.Ю. C1-142 Еремина Т.В. C1-51 Ермак... О.Е. C5-231 Запуниди С.А. C3-36 Заремский М.Ю. C1-19, C1-76, C1-142..., C3115, C3-51, C5-118, C5-139, C5-145, C5-151, C5-164, C5200 Иванов...-52 Иванов Р.В. 130, 142, C375 Иванова А.В. C5-97 Иванова В.О. C5-38, C5131 Иванова... Р.С. C1-105 Кожунова Е.Ю. C5-108, C5-169 Козлов А.В. C5-109, C5-231 Козлов В.В. C1...-33, C4-86, C5-133, C5-157, C5-204 Косточко А.В. C5-40, C5135 Костюк...-77, C5-5, C5-205 Курмаз С.В. C1-117, C4-57, C5-101, C5-125, C5-197...-28, C4-29 Лозинский В.И. 130, 142, C2-15, C2-38, C3..., C1177 Макарова Е.Н. C5-56 Макарова Л.И. C5-46, C5166, C5-32 Макарова М.А. C5-47 Маковецкий..., C5-130 Марк С. 105 Маркелов Д.А. C5-142, C5143 Маркин А.В. 209, C5-93, C5-144, C5-208...-163 Масленникова Т.П. C5-83, C5-191 Мастюгин А.В. C5-189 Матвеев В.К. C5-240 Матвеева И.А. C4... Н.Г. C5-38, C5131, C5-132 Матнишян А.А. 270 Матусевич Ю.И. C5-87, C5-263 Матухин Е.Л. C5-40... В.С. 229, 242, 284, C5-155, C5-184, C5-253 Молькин В.Е. C5-186 Монаков Ю.Б. 97... Морозов П.В. C5-156 Москалев И.В. C5-47 Москаленко Ю.Е. C5-150 Москвин Ю.Л. C5-160 Москвина М.А. C5-238..., C4-79, C5-6, C5-109, C5140, C5-160, C5-185, C5208, C5-241 Мукменева Н.А. C3...-67 Никулова У.В. C5-168 Нилов Д.Ю. C5-217 Нистратов А.В. C5-77, C5106, C5-196 Нифантьев...-155, C5-77, C5106, C5-170, C5-171, C5183, C5-192, C5-196 Новакова А.А. C5-169..., C1-177, C5-32, C5-33, C5-36, C5-42, C5-166, C5-248 Паращук Д.Ю. C3... Романов C.А. - C1-142, C1143 Романов Г.А. - C5-44 Ронова И.А. 226, C5-204, C5-219 Рощупкин..., C5-161 Смирнова Л.Г. C5-214 Смирнова Н.М. 136 Смирнова Н.Н. C5-127, C5-144, C5-208, C5-215... Н.П. C4-4 Солдатов В.С. C5-220 Соловова Ю.В. C5-262 Соловская Н.А. C5-223 Соловцова О.В. C5-221 Соловьев... М.В. 177 Тарабукина Е.Б. 228, C5-6, C5-109, C5-231 Тарасевич К. C5-3 Тарасов А.Е. C1-169 Тарасюк...-15 Темнов Д.Э. 247, C5-27, C5-232, C5-243, C5-244 Тепляков В.В. C3-56... Филиппов A.П. 103, 228, 269, C5-6, C5-109, C5-212, C5-231 Филиппов А.Н. C1-178..., C1-13, C2-3, C5-119, C5-120, C5-155, C5-184 Финкельштейн Е.Ш. 106, C1...-14, C5-30, C5-31, C5-66, C5126, C5-168, C5-182, C5193, C5-222 Чапурина..., C5-80, C5-113, C5140, C5-156, C5-191, C5224, C5-235, C5-264 Челушкин П.С. C5-76, C5100, C5-138 Червинский Т.И. C1-193 Червятина М.Е. C5... В. C5-254, C5-255 Шилова И.А. C5-256 Шилова С.В. C3-10 Шинкарев С.М. C5-221 Шипина О.Т. C5... Л.М. 250, 276, C5-7, C5-81, C5-205, C5207, C5-268 Ясина Л.Л. C5-43, C5-138 Ясногородская...



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0.11/5
... 116/C2 116/A3 115/C5 095/B8 095/C1 087... 220/A4 078/A3 077/C5 078/A4 077/C7 078... 060/C3 060/C4 060/C5 060/C2 060/C7 061... 144/C8; 145/A1144/C5 045/C5 045/C6 6897 6900 4357.../Fisch 051/B5 051/C2-C5 051/B2-B4 051/B1... 104/B4 104/B6 103/C5-C8 103/C1-C3 Catalog...; C1 099/C2 099/C3-C5 099/C6 099/B7 099.../B8; Cl 3143a 102/C2-C5 102/C6 102/A6-A7.../A5 058/A3-A4 042/C5 219/C5 219/C6 3132 3115... 235/C2 235/C3 235/C5 235/C4 235/C6 235/C7 235/C8 215/C5 215/C6 215/C7 215...-C7 125/B7-B8 125/C5-C6 1768 1772 1766 1767... 6273 6272 1.93/C6 193/C5 193/C7 193/C4 193.../C3-C4 218/C1 180/C5 3778 3762a 3762b 127/A1... 194/B6-B7 194/C3-C5 194/B5 3752 6283 5738... 185/C6 185/C7 185/C5 189/C7 189/C8 190.../C2 181/C8 181/C5-C7 197/C4-C5 198/A7 197... 177/C1 177/C3 192/C5 192/C8 193/A5 193... 184/C6 184/C4 184/C5 6057 6048 6060 6060a 6060b... 5982 5958 186/B8 186/C5 186/A3 186/B1-B2.../A3-A6__ 178/C4 178/C5-C6 178/C7-C8 5666... 181/B5 192/A7 191/C5 192/A5 191/C6 191.../A7-A8; B1 177/C4-C5 5635 5633 5634 5726 5729... 199/C8 199/C7 198/C5 183/B8 199/C2 199/C3 199/C1 Catalog _ _ 218/C5 218/C6 192/C3 176... 175/C7-C8 175/C3-C5 6485a 6483 6937 6938 6228.../C8 190/C2-C3 190/C5 6258 6253 6255 6503 6502... 176/C2-C3 176/C4-C5 6161 6162 6150 6160 5624... 188/B2-B4 188/C4-C5 6072a 6072b 6068 6071 6074.../C6-C7 075/C4 232/C5 105/C5 106/A3 105/A7... Frame/Fisch Catalog 4677 1531C3-C5 153/C6-C7 153/C8... 4519a 148/Al 4533 147/C5 148/A2 147/C8 147... 146/C7 146/C8 146/C5-C6 4521 4534 4532 4520...-B5 209/A3-A4 212/C5 2121C6 207/B4-B5 215.../A3-A4 013/C4 013/C5 0364a 013/C6 013/C7...-B 0400c 014/C6-C8 015/C5 399 413 015/B8; Cl... 016/Al 015/C4 014/C5 015/C2 015/C7 015... 2801 Frame/Fisch 094/C4-C5 094/C7-C8 094/B8.../B6-B7 049/C4 049/C5-C6 Catalog Familia Ericaceae Ericaceae...-B3 095/A1-A3 093/C5-C8; 094/ 094/A2-A3.../A6-A7 109/A6 109/C5 2976 2981 2972 2972a 2971... 220/B4 220/C4 220/C5 220/C6 221/C7 220... 768 035/C8_ 035/C3-C5 035/C6-C7 235/A7...; Cl 020/C2-C4 020/C5 020/84 020/B3 023... 023/B2-B4 nutans 022/C5-C8; 023// praecox 0548a 023/A3 praecox 021/C4-C5 subspicata 0542b 022/A1-A3.... M.Thunb. 234/A5 barbatum 233/C5 distachyum 233/C8 hirtum 234... Frame/Fisch 031/C2 031/C5-C6 031/C7 031/C8... 0636a 030/C6-C7 030/C5 0620a 029/B5-B6 029... 029/C3-C4 0622a 029/C5 0624d 030/A8 030/C3... 026/C7 026/C4 026/C5 442 599 598 0598a 596.../C8 234/C2-C3 234/C5-C6 234/C4 7332a 234... 645 031/86 682 032/C5-C8; 033/) 681 032/C4... 457 zizanoides (Andropogon muricat 016/C5 Species murinum murinum murinum (rigidum... 034/B7 034/B8 034/C5-C6 034/C8 0571a 035... floridanum officinalis Frame/Fisch 206/C5-C6 058/B4-B7 6827...; Cl 1579a 058/C2 058/C5-C6 058/C3 058/C4 124/B5 174/C4 174/C5 1584 1580 1582 3725 5558.../A7 059/C8 059/C4-C5 059/C6-C7 _ 2428-_ 2434... 084/C6 2483d 084/C3-C5 082/A5 084/C1-C2... 082/C3 082/C4 082/C5-C8 2477 2471 2471a 2471b... 135/A7 4067 138/C4-C5 4033 136/A6-A8 4032.../C8; 138/A14053 137/C4-C5 4059, 137/C8 134/A8... 176 4022 4023 1351C4__ 135/C5 135/C6-C7 135/C3...-C 4018a 4181 141/C2 141/C5-C6 141/C3 141/68... 139/C5-C7 139/C8 139/C3 139/C4 142/A8 142/A4 142...-B7 008/C2-C4 008/C5-C7 008/81 0193a 195... 4042 4039 4040 1421A1 142/A3 141/C7 142/A2 136/B8.../C6 136/C2-C4 136/C5 139/A2 4083a 4083 4094.../A3-A5__ 139/A6 134/C5-C7 134/C8 134/6465...-C 135/Al 135/A2 140/C5 140/C6 141/Al-A2... 170/A2 092/B8 170/C5 092/C2 5404a 2846 5438.../A8 5341 5321 168/C3-C5 169/B8 5301 5377 169... 238/A8 237/C5 237/C6-C7 163/C5 165/A8 165... 075/B8 074/C4 074/C5 2150a 075/B6-B7 2151b.../B5 160/C4 4877a 160/C5-C6 160/C7 161/B4... 3478a 110/C4 110/C5-C6 110/C5-C6 224/C6-C7... 7464b 238/C3-C6 002/C5 002/C6-C7 0043a 003.../Fisch 202/C7 6652a 202/C5 146/A2 146/A3 146...; B1 B1 204/A4 204/C5 204/C6-C8 6732a 203.../Fisch 039/C3 039/C4-C5 039/B4-B8; C1-C 041.../A3-A4 0908b 040/C4-C5 0914a 040/C6-C7 040... 223/A1-A3 7011 a 222/C5 074/C1 074/C1 2128a... 2820a 091/C3-C4 091/C5-C6 086/A3-A4 086...-B7 085/B8 2514a 085/C5 086/A7-A8; B1-B; B1.../A3-A4 047/C3 047/C5 047/C6 1112a 11 12a... 112/C2-C3 112/C4-C5 112/C6-C8 Catalog 3645... 111/C4 3489a 3489b 111/C5-C6 115/C3 115/C4... 116/C8; 116/C4 116/C5 117/A2 3588a 117/A3...-A8;131-1 B1-B: 3: 037/C3-C5 038/C3-C6 038/C7... 7141c 227/A8 7141d 228/C5 228/B4-B7 7147a 7147b.../C7-C8; 231/> 230/C4-C5 7157a 7157C 231/A2-A4... 229/C2-C4 7153b 229/C5-C7 7153e 7153c 1657 1356.../B6-B7 7156b 227/C4-C5 7130a 225/A6 225/A7.../A8 7130c 7130e 225/C4-C5 7130i 7130Î 225/B2-B3... 301 5a 3015a 0951C5 095/C5 096/C5-C6 096/A3-A6... 301 9a 096/B3 098/C5 3048a 098/C6-C7 3048c.../A5 143/81-B2 142/B1-B2 142/B3 007/B4-B5.../81 144/B2 144/A8 142/C7 142/C8 143/C7 144.../C3 144/B3 145/C5 142/B4-B5 142/B7 4301 4308 4303... 145/C3 142/B6 142/C2-C3 142/C4 142/C6 142/C5 142/B8 142/C1 041.../B7 005/C3-C4 005/C5 0918a 4332 4337 4331 4339... 006/B6 007/A6 231/C5 china? 232/Al excelsa herbacea...-C3 089/C6-C8 089/C5 089/C4 127/A8 3310a... Frame/Fisch 063/C7 063/C5-C6 071/C3-C6 069... 065/C8 065/C7 065/C5-C6 Catalog 1792g 1792f 2042...-B2 070/A6-A8 068/C5 068/C6 068/C4 - 1987...-C8; 071// 071/B6 070/C5-C6 071/B3-B5 071... 007/C8 007/C6 007/C5 007/C4 007/C7 2019... 201/Al 200/C4 200/C5 200/C8 200/C7 1902.../Fisch 241/C2-C4 241/C5 241/C6-C8 241/A8... 7763b 7763c 246/A2 245/C5 246/A3 245/C4 245... 265/C4 265/B3 265/C5-C6 265/B4 8063 8077... san uineus Pagina 73 267/C5 267/C1 267/C4 267...



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0.12/5
... 137 3.2.3 Chemical reactivity of germylenes 142 3.2.3.1 Oxidative reactions with sulfur and selenium 142 3.2.3.2 Cycloaddition reaction with o-quinone 148... 12.7 to 5.0 Hz (C2,8 to C5) in the case of 6a... 15.5 to 2.0 Hz (C2 to C5) for compound 7a. If we..., in CDCl3) 2 6a 3 CH3 CH C5 C3,7 C4,6 22.87 45... CDCl3) CH3 CH C7 C3 C5 C4 C6 C2 C8 1 21... 133.40 140.69 and 142.56 150.00 and 158..., 130.85 34 140.90, 142.56 Chapter I Pnictogenium cations: syntheses...), 121.66 (C3), 128.17 (C5), 136.11 (C6), 137.01....72 (CH-CH3), 109.73 (C5), 116.98 (C3,7), 46 Chapter... 129.96 (C3,7), 133.82 (C5), 140.78 (C4,6), 177.63..., C3,7), 136.99 (d, 5JCP = 5.0 Hz, C5), 144.56 (d, 4JCP = 5.7 Hz, C4...), 115.80 (C3,7), 125.09 (C5), 49 Chapter I Pnictogenium cations: syntheses..., C3), 138.79 (d, 5JCP = 2.0 Hz, C5), 143.55 (d, 4JCP = 2.6 Hz, C6..., 130.85 (C3,5,7), 140.90, 142.56 (C4,6), 155.33 (C2... of 8 (0.34 g, 50 %, mp 138-142 °C). 1 H NMR (300 MHz, CDCl3): ppm...), 121.99 (C3,7), 130.00 (C5), 139.97 (C4,6), 158.78... (C3), 133.40 (C5), 140.69 and 142.56 (C4,6), 150.00...), 121.05 (C3,7), 127.46 (C5), 138.39 (C4,6), 162.17... 123.05 (C3,7), 127.41 (C5), 136.97 and 138.35...), 115.98 (C3,7), 125.31 (C5), 139.35 (C4,6), 150.63...), 117.47 (C3,7), 127.10 (C5), 140.20 (C4,6), 150.70..., in CDCl3) CH3 CH CF3 C5 C4,6 C3,7 C2,8 6a 21... (d, JCP = 12.8) 133.54 (d, JCP = 2.7) 4 142.82 (d, JCP = 2.7) 3 121.95 (d, JCP... = 3.8) 132.55 3 3 21.24 (d, JCP = 1.3) C5 136.99 (d, JCP = 5.0) 5 C4,6 144....61 47.21 131.63 142.30 120.63 (d, 3 JCP = 9.1) 151... (d, 2JCP = 10.7) The 1H and 142.83 140.55 13 C{1H..., C3,7), 136.94 (d, 5JCP = 5.3 Hz, C5), 143.95 (d, 4JCP = 4.9 Hz, C4..., C3,7), 133.54 (d, 5JCP = 2.7 Hz, C5), 142.82 (d, 4JCP = 2.7 Hz, C4,6), 155...), 124.46 (C3,7), 134.08 (C5), 141.52 (C4,6), 157.95...), 122.39 (C3,7), 129.82 (C5), 139.10 (C4,6), 161.14...), 117.49 (C3,7), 127.12 (C5), 140.18 (C4,6), 150.63... (d, 3JCP = 9.8 Hz, C3,7), 139.14 (C5), 146.82 (C4,6), 149.91...), 120.93 (C3,7), 132.55 (C5), 142.83 (C4,6), 150.48 and...), 119.58 (C3,7), 130.73 (C5), 142.23 (C4,6), 149.88 and... (d, 3JCP = 7.4 Hz, C3,7), 127.90 (C5), 140.47 (C4,6), 150.54... (d, 3JCP = 7.5 Hz, C3,7), 128.58 (C5), 140.43 (C4,6), 150.88... (d, 3JCP = 6.6 Hz, C3,7), 132.17 (C5), 141.87 (d, 4JCP = 6.4 Hz, C4... yellowish crystals of 23 (mp 142-145 °C). 103 Chapter II Pnictogenium... (d, 3JCP = 6.5 Hz, C3,7), 128.74 (C5), 140.55 (C4,6), 150.83...), 125.57 (C3), 133.93 (C5), 141.43 (C6), 144.86...), 125.55 (C3), 131.57 (C5), 140.87 (C6), 143.55... = 10.6 Hz, C3,7), 135.62 (C5), 137.95 and 141.05... the product 26B (mp 140-142 °C). 31 P {1H} NMR (121 MHz....27 (C6H2, CH), 125.04 (C5), 127.20 and 128.00... (C6H2 quat), 136.81 and 142.77 (C6H2 quat), 138.74... (d, 3JCP = 5.7 Hz, C3,7), 132.39 (C5), 141.70 (C4,6), 153.63... (d, 3JCP = 4.7 Hz, C3,7), 133.22 (C5), 143.37 (C4,6), 154.06... 63.23 63.22 C3,7 C5 104.31 and 103.89... coupling constant between H5-P and C5-P can be observed (6JHP = 2.9 Hz...) CH3 CH2 NCH2 CH C3,7 C5 C4,6 32 22.72 - 48... 139.62 and 139.89 142.93 and 144.90 (d, 4 JCP... for the aromatic protons (Table 7). 142 Chapter III Bridged bis(pnictogenium... ppm, in CDCl3) CH3 CH C5 C4,6 C3,7 C2,8 49 23... 112.58 (C3,7), 117.42 (C5), 133.14 and 132.63... 111.04 (C3,7), 116.71 (C5), 132.14 and 132.49... 112.21 (C3,7), 117.44 (C5), 132.63 and 133.12... 110.98 (C3,7), 116.99 (C5), 132.42 and 132.79... 112.71 (C3,7), 118.52 (C5), 133.83 and 134.20... 111.19 (C3,7), 116.97 (C5), 132.50 and 132.85...), 108.70 (C3), 122.52 (C5), 128.80 (C7), 158 Chapter... 103.89 (C3,7), 105.23 (C5), 129.62 and 129.22... 106.19 (C3,7), 107.22 (C5), 131.25 and 131.60... 128.20 (C3,7), 135.98 (C5), 143.09 and 144.64... 128.20 (C3,7), 136.27 (C5), 143.52 and 144.53... 123.05 (C3,7), 136.80 (C5), 140.67 and 141.06... (d, 3JCP = 5.1 Hz) (C3,7), 135.99 (C5), 142.93 and 144.90 (d, 4JCP...) (C3,7), 136.09 (d, 5JCP = 4.6 Hz, C5), 143.09 (d, 4JCP = 4.3 Hz), and... 128.94 (C3,7), 136.09 (C5), 143.09 and 144.84... 123.68 (C3,7), 131.59 (C5), 140.42 and 141.48... 123.59 (C3,7), 131.48 (C5), 140.40 and 141.38... 118.96 (C3,7), 127.31 (C5), 139.88 and 141.06... 118.59 (C3,7), 127.09 (C5), 139.77 and 140.68... 117.87 (C3,7), 126.56 (C5), 139.62 and 139.89... 116.61 (C3,7), 124.29 (C5), 137.40 and 137.54... 116.33 (C3,7), 123.69 (C5), 137.13 and 137.19...), 115.70 (C3,7), 123.00 (C5), 136.80 (C4,6), 160.50...), 115.50 (C3,7), 122.00 (C5), 136.60 (C4,6), 160.60...), 120.41(C3), 123.54 (C5), 127.55 (C7), 138.12...), 122.90 (C7), 126.08 (C5), 137.55 (C6), 138.04...), 120.67 (C3), 124.12 (C5), 128.39 (C7), 138.74... (152 mg, 92 %, mp 140-142 °C (dec.)). 176 Chapter III Bridged...), 117.24 (C3,7), 126.63 (C5), 139.13 (C4,6), 150.60... studies and reactivity 126.80 (C5), 138.92 (C4,6), 155.70...), 116.29 (C3,7), 124.69 (C5), 137.16 (C4,6), 132.69....42 (C5), 129.05 (C7), 133.15, 140.95, 142.50, 146... 119.07 (C3), 125.98 (C5), 133.36 (C-C(CH3)3), 137.64... and 140.49 (C-C(CH3)3), 142.65, 142.77 and 147.18 (C-O), 153...), 118.54 (C3), 125.37 (C5), 133.02 (C-C(CH3)3), 137.65..., 117.82 (C3,7), 126.42 (C5), 138.34 and 138.97..., 118.21 (C3,7), 126.61 (C5), 138.64 and 138.74...



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0.18/5
...-H), 7.67 (d, J=8.4 Hz, 2H, C3′- and C5′-H), 7.39 (dt, J=9.0, 1.2 Hz, 1H, imidazolyl... (dt, J=9.0, 1.2 Hz, 1H, imidazolyl C6-H / C5-H), 7.22 (m, 3H, C2′-, C6′-, C7....1 (C2, C6), 132.6 (C3, C5), 129.6 (C3′, C5′), 126.5 (C2′, C6′), 124..., CDCl3) δ: 7.58 (d, J=8.3 Hz, 2H, C3-, C5-H), 7.50 (d, J=8.3 Hz, 2H, C2-, C6... (d, J=8.2 Hz, 2H, C3′-, C5′-H), 7.17-7.11 (m, 2H, imidazolyl C5-, C6-H), 7.01 (d, J=7.7 Hz...), 142.5 (C3a), 135.5 (C7a), 135.4 (C1), 132.3 (C3, C5), 132.1 (C3′, C5′), 130... MHz, CDCl3) δ: 7.64 (s, 1H, furyl C5-H), 7.56 (s, 1H, imidazolyl C4-H), 7.36 (s, 1H, furyl C5'-H), 7.26 (s, 1H, imidazolyl C7-H), 7.18....7 (furyl C2), 143.7 (furyl C5), 143.2 (C2'), 142.5 (furyl C5'), 141.6 (C3a), 134.1 (C7a), 132.6 (C6), 131.9 (imidazolyl C5), 119....7 (-NCH2), 20.7 (C6-CH3), 20.3 (C5-CH3). MS: m/z (%): 293.1 (M+1) (100), 294..., 1H, C4'-H), 7.20-7.12 (m, 3H, C5-H, C5'-H and C6'-H), 7.05 (t, J=7.5 Hz, 2H, imidazolyl C5-H and C6-H), 6.63 (d, J=7.5 Hz, 1H... NMR (75MHz, CDCl3) δ: 150.6 (C2), 142.3 (C3a and C7a), 134.5 (C1....9 (C3), 127.8 (C3'), 127.0 (C5), 126.9 (C5'), 123.3 (imidazolyl C6), 123.1 (imidazolyl..., imidazolyl C4-H), 7.70 (s, 1H, furyl C5-H), 7.62 (s, 1H, C7-H), 7.38 (s, 1H....5 (furyl C5), 143.0 (C5'), 142.4 (C3a), 134.8 (C7a), 127.2 (C6), 127.1 (imidazolyl C5), 120... C6-H), 7.24-7.22 (m, 3H, imidazolyl C5-H, C6-H and C7-H), 6.91 (d, J=8.1Hz, 1H, C5-H), 6.79 (d, J=8.4 Hz, 1H, C5'-H), 6.65-6.61 (m, 2H, C2... C2), 142.7 (C3a), 136.1 (C7a), 128.9 (C1), 122.7 and 122.5 (C5 and....5 (C6'), 118.0 (C6), 112.2 (C5'), 111.4 (C5), 110.9 (C2), 110.10 (C2... C7-H), 7.23-7.17 (m, 2H, imidazolyl C5-H and imidazolyl C6-H), 7.11 (d, J=3.0 Hz....4 (C2), 153.3 (C5), 151.7 (C2'), 151.5 (C5'), 150.6 (imidazolyl C2), 142.2 (C3a), 135....0 (furyl C2), 144.0 (furyl C5), 143.2 (C2'), 142.6 (furyl C5'), 142.0 (C3a), 135.1 (C7a...), 123.3 (imidazolyl C6), 123.2 (imidazolyl C5), 113.0 (furyl C3), 112.0 (furyl... C6-H), 7.09-6.99 (m, 3H, C5'-H, C6'-H and imidazolyl C5-H), 6.87 (qd, J=9.0 Hz...), 142.1 (C3a), 138.8 (C1), 135.7 (C7a), 131.6 (C1'), 130.3 (C5), 130.2 (C5'), 129...), 123.1 (imidazolyl C6), 123.0 (imidazolyl C5), 120.0 (C6), 117.3 (C4), 117....4 (C2), 150.4 (C5), 149.5 (C2'), 149.0 (C5'), 148.5 (imidazolyl C2), 142.4 (C3a), 135...'), 122.9 (imidazolyl C6), 122.8 (imidazolyl C5), 122.1 (C4), 118.2 (C6), 112...), 142.6 (C3a), 135.4 (C7a), 130.7 (C2 and C6), 127.5 [imidazolyl (C5 and...'-H), 6.85 (d, J=8.6 Hz, 2H, C3'-H and C5'-H), 5.32 (s, 2H, -NCH2), 3.83 (s, 3H...'-H and C6-H), 7.66-7.61 (m, 2H, C5-H and imidazolyl C4-H), 7.53 (t, J=8.0 Hz, 1H, C5'-H), 7.35 (d, J=7.7 Hz, 1H, C6'-H), 7.00...), 131.7 (C6'), 130.5 (C5), 130.1 (C4), 124.4 (C5'), 123.7 (imidazolyl C4), 123...-H), 6.90 (d, J=8.4 Hz, 1H, C5-H), 6.81 (d, J=8.4 Hz, 1H, C5'-H), 6.67-6.62 (m, 2H, C2...), 132.1 (imidazolyl C6), 131.5 (imidazolyl C5), 129.4 (C1), 122.8 (C1'), 121....8 (C6), 118.1 (C6'), 112.3 (C5), 111.6 (C5'), 111.0 (C2), 110.3 (C2'), 109...) δ: 153.5 (C2), 153.4 (C5), 151.8 (C2'), 151.2 (C5'), 150.7 (imidazolyl C2), 141...), 131.6 (imidazolyl C6), 130.7 (imidazolyl C5), 126.1 (C1), 120.6 (C1'), 119...-7.20 (m, 2H, C2'-H and C5-H), 7.13 (t, J=7.8 Hz, 1H, C5'-H), 6.95 (s, 1H, C7... (m, 3H, imidazolyl C7-H, C3'-H and C5'H), 5.32 (s, 2H, -NCH2), 2.39 (s, 3H....54 (C3'), 127.02 (C5), 126.79 (C5'), 120.26 (imidazolyl C4... C2), 142.4 (C3a), 135.2 (C1), 134.2 (C7a), 132.6 (C3 and C5), 132....0 (C2), 153.7 (C5), 153.5 (C2'), 151.6 (C5'), 150.8 (imidazolyl C2), 142.5 (C3a), 134.7 (C7a), 126.4 (imidazolyl C6), 126.0 (imidazolyl C5), 124..., J=9.0 and 1.8 Hz, 2H, C3'-H and C5'H), 7.28 (s, 1H, C7-H), 6.98 (d, J=8.4 Hz... MHz, CDCl3) δ: 154.7 (imidazolyl C2), 142.2 (C4), 137.0 (C3a), 135.0 (C1...'), 127.6 (imidazolyl C6), 127.3 (imidazolyl C5), 127.3 (C1'), 127.1 (C3' and... MHz, CDCl3) δ: 153.4 (imidazolyl C2), 142.2 (C3a), 134.1 (C1), 134.0 (C7a...'), 127.4 (imidazolyl C6), 127.0 (C5'), 126.9 (imidazolyl C5), 121.4 (imidazolyl C4), 111...), 142.1 (C3a), 137.4 (C1), 135.0 (C7a), 133.6 (C4), 132.3 (C2), 131.6 (C5...'-H), 7.20-7.11 (m, 3H, imidazolyl C5-H, C6-H and C5'-H), 7.03 (dd, J=9.0 and 0.9 Hz...) δ: 151.5 (imidazolyl C2), 143.5 (C3a), 142.0 (C7a), 138.4 (C1), 132.9 (C4....0 (imidazolyl C4), 130.6 (C5), 130.1 (C4'), 130.1 (C5'), 129.5 (C2'), 127.5 (C1...'), 123.5 (imidazolyl C6), 123.4 (imidazolyl C5), 123.1 (C3), 122.8 (C3'), 107...-H), 6.92 (d, J=8.2 Hz, 1H, C5-H), 6.83 (d, J=8.1 Hz, 1H, C5'-H), 6.61 (m, 2H, C2'-H and...), 142.4 (C3a), 135.6 (C7a), 128.1 (C1), 126.8 (imidazolyl C6), 126.7 (imidazolyl C5....8 (C6), 118.0 (C6'), 112.2 (C5), 111.7 (C5'), 111.6 (C2), 111.1 (C2'), 108...) δ: 7.12-7.06 (m, 4H, C2-H, imidazolyl C5-H, imidazolyl C6-H and C7-H), 6.98...-H), 6.89 (d, J=9.0 Hz, 1H, C5-H), 6.74 (d, J=8.7 Hz, 1H, C5'-H), 6.69 (dd, J=8.7 and 3.0 Hz...'), 151.2 (C3'), 150.8 (imidazolyl C2), 142.5 (C3a), 135.1 (C7a), 129.7 (C1...), 122.5 (imidazolyl C6), 122.4 (imidazolyl C5), 120.6 (C1'), 117.3 (C6), 117.2 (C6'), 114.5 (C5), 112.6 (C5'), 112.3 (C2), 110.9 (C2'), 108...



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❉✉r❤❛♠ ❊✲❚❤❡s❡s ❚❡tr❛✢✉♦r♦♣②r✐❞❛③í♥❡✿ ❛ s❝❛✛♦❧❞ ❢♦r t❤❡ s②♥t❤❡s✐s ♦❢ ❤✐❣❤❧② ❢✉♥❝t✐♦♥❛❧✐s❡❞ ❤❡t❡r♦❝②❝❧❡s P❛tt✐s♦♥✱ ●r❛❤❛♠ ❍♦✇ t♦ ❝✐t❡✿ ❚❡tr❛✢✉♦r♦♣②r✐❞❛③í♥❡✿ ❛ s❝❛✛♦❧❞ ❢♦r t❤❡ s②♥t❤❡s✐s ♦❢ ❤✐❣❤❧② ❢✉♥❝t✐♦♥❛❧✐s❡❞ ❤❡t❡r♦❝②❝❧❡s✱ ❉✉r❤❛♠ t❤❡s❡s✱ ❉✉r❤❛♠ ❯♥✐✈❡rs✐t②✳ ❆✈❛✐❧❛❜❧❡ ❛t ❉✉r❤❛♠ ❊✲❚❤❡s❡s ❖♥❧✐♥❡✿ P❛tt✐s♦♥✱ ●r❛❤❛♠ ✭✷✵✵✽✮ ❤tt♣✿✴✴❡t❤❡s❡s✳❞✉r✳❛❝✳✉❦✴✷✾✷✼✴ ❯s❡ ♣♦❧✐❝② ❚❤❡ ❢✉❧❧✲t❡①t ♠❛② ❜❡ ✉s❡❞ ❛♥❞✴♦r r❡♣r♦❞✉❝❡❞✱ ❛♥❞ ❣✐✈❡♥ t♦ t❤✐r❞ ♣❛rt✐❡s ✐♥ ❛♥② ❢♦r♠❛t ♦r ♠❡❞✐✉♠✱ ✇✐t❤♦✉t ♣r✐♦r ♣❡r♠✐ss✐♦♥ ♦r ❝❤❛r❣❡✱ ❢♦r ♣❡rs♦♥❛❧ r❡s❡❛r❝❤ ♦r st✉❞②✱ ❡❞✉❝❛t✐♦♥❛❧✱ ♦r ♥♦t✲❢♦r✲♣r♦✜t ♣✉r♣♦s❡s ♣r♦✈✐❞❡❞ t❤❛t✿ • ❛ ❢✉❧❧ ❜✐❜❧✐♦❣r❛♣❤✐❝ r❡❢❡r❡♥❝❡ ✐s ♠❛❞❡ t♦ t❤❡ ♦r✐❣✐♥❛❧ s♦✉r❝❡ • ❛ ❧✐♥❦ ✐s ♠❛❞❡ t♦ t❤❡ ♠❡t❛❞❛t❛ r❡❝♦r❞ ✐♥ ❉✉r❤❛♠ ❊✲❚❤❡s❡s • t❤❡ ❢✉❧❧✲t❡①t ✐s ♥♦t ❝❤❛♥❣❡❞ ✐♥ ❛♥② ✇❛② ❚❤❡ ❢✉❧❧✲t❡①t ♠✉st ♥♦t ❜❡ s♦❧❞ ✐♥ ❛♥② ❢♦r♠❛t ♦r ♠❡❞✐✉♠ ✇✐t❤♦✉t t❤❡ ❢♦r♠❛❧ ♣❡r♠✐ss✐♦♥ ♦❢ t❤❡ ❝♦♣②r✐❣❤t ❤♦❧❞❡rs✳ P❧❡❛s❡ ❝♦♥s✉❧t t❤❡ ❢✉❧❧ ❉✉r❤❛♠ ❊✲❚❤❡s❡s ♣♦❧✐❝② ❢♦r ❢✉rt❤❡r ❞❡t❛✐❧s✳ ❆❝❛❞❡♠✐❝ ❙✉♣♣♦rt ❖✣❝❡✱ ❉✉r❤❛♠ ❯♥✐✈❡rs✐t②✱ ❯♥✐✈❡rs✐t② ❖✣❝❡✱ ❖❧❞ ❊❧✈❡t✱ ❉✉r❤❛♠ ❉❍✶ ✸❍P ❡✲♠❛✐❧✿ ❡✲t❤❡s❡s✳❛❞♠✐♥❅❞✉r✳❛❝✳✉❦ ❚❡❧✿ ✰✹✹ ✵✶✾✶ ✸✸✹ ✻✶✵✼ ❤tt♣✿✴✴❡t❤❡s❡s✳❞✉r✳❛❝✳✉❦ ✷ ~'Durhatn University A Thesis Entitled Tetrafluoropyridazine: A Scaffold for the Synthesis of Highly Functionalised Heterocycles The <'Opyrighl of thl• thcol• rest& with tbc author or lhe university to which h wa." subrnincd. No quot•tlon from it, or information derived tlom h may be published whbout the prior wriuen consent of the author or uniYersity, and any information derived rrom it ahould be acltoowl > Cl- Br > I provides further evidence for the above mechanism9 • It is well established that the bond strength of C-X bonds decreases in the order C-F > C-CI > C-Br > C-1 and, therefore, the high reactivity of fluorine towards nucleophilic displacement suggests that bond breaking does not occur in the rate determining step. Consequently, addition of the nucleophile must be rate determining. This step is accelerated in more electron deficient heterocycles, which is supported by the fact that fluorine is the most electronegative ofthe halogens. 3 Chapter 1: The Synthesis and Chemistry of Pyridazine Derivatives The preference for substitution a- and y- to ring nitrogen in halogenated heteroaromatic derivatives can be explained by the stability of the corresponding Meisenheimer intermediates2 (Scheme 1.5). The negative charge can be stabilised via delocalisation onto the electronegative ring nitrogen for a- and y-substituted systems, but this is not possible when the halogen atom is P- to ring nitrogen. Substitution, therefore, proceeds via the most stable Meisenheimer intermediate. a-to Ring Nitrogen P-to Ring Nitrogen uaxN X ~ N e N Q-x crNuc ~ N N6 6 I N Nuc Nuc N X y-to Ring Nitrogen u ()_Nuc ~ X ~ Nuc .. ) X ~0 ~ N) Nuc 6 N Scheme 1.5 1.1.2 The Diazines This thesis is concerned with the production of highly functionalised pyridazine systems from tetrafluoropyridazine, so a brief discussion of diazine chemistry is appropriate before pyridazines are considered in more detail. The structures of the three diazines (pyridazine, pyrimidine and pyrazine) consist of two nitrogen atoms in a six membered aromatic ring (Figure 1.2). 0 N N Pyridazine e ) N N Pyrimidine N () N Pyrazine Figure 1.2 4 Chapter 1: The Synthesis and Chemistry of Pyridazine Derivatives The basicity of the diazines is reduced, relative to pyridine, due to the electron withdrawing effect of the second ring nitrogen destabilising the protonated cation. Of the three diazines, pyridazine is the most basic, this is hypothesised to be due to the 'alpha effect' whereby reduced repulsion of the two adjacent nitrogen lone pairs slightly stabilises the protonated form 10 • Diazines are correspondingly more reactive towards nucleophilic substitution than pyridine systems, due to the additional electron withdrawing effect of the second ring nitrogen 2 • Again, sites a- and y- to ring nitrogen are activated towards nucleophilic attack, in other words, all sites in diazines are activated except for the 5-position of pyrimidines. Therefore, halogen substituents at both the 3- and 4-positions in pyridazine derivatives are expected to be highly reactive towards nucleophilic displacement. The diazines are less reactive towards electrophiles than pyridine derivatives, which is reflected in their lower basicity. In general, electrophilic attack occurs via addition to ring nitrogen to give diazinium cations. Addition to both ring nitrogens is generally extremely difficult as this would result in the formation of a dication 10, although it is possible with powerful alkylating agents such as trialkyloxonium salts (Scheme 1.6) 11 • Electrophilic substitution at carbon in diazines is rare, although some halogenation reactions are known, requiring extremely forcing conditions. 0 0Me3 + BF 4- N N 0 Me~N NGl I Me 10,21% 9 Scheme 1.6 1.1.3 Oxy-heteroaromatics Oxy-pyridines and oxy-diazines generally exist as the keto tautomer, and are known as pyridones or diazinones. The pyridone tautomer is ...



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...%), либо смеси двух продуктов с соотношением 142:143 от 1:1.5 до 5:1 и суммарным выходом... α,β-ненасыщенных карбонильных соединений и других нуклеофилов [142]. Для всех реакций характерны те... находятся в фиксированных положениях при δ ~ 133 (C5), 147 (C4), 157 (C6) и 162... (=CH–Si), 146 (C2), 152 (C5) и 184 (C3) м.д. в спектрах ЯМР 13C..., расположенные при δ ~ 95 (С3) и 148 (C5) м.д., а также самый слабопольный сигнал при....8 (C ); 124.3 (CoB); 126.5 (C4); 126.7 (C5); 127.1 (CпA); 128.5 (CoA); 131....9, 114.5 (CмA,B); 120.8 (CoA); 123.8 (C5); 124.0, 126.4, 133.1, 133.3 (CиA...); 146.7 (Cп) м.д. Сигналы атомов C4 и C5 не видны из-за сильного....5 (C≡C); 121.2 (C4); 123.8 (Cм); 125.5 (C5); 126.9 (Cо); 134.8 (C3); 139...); 123.9 (Cм), 126.6 (Co); 127.8 (C5); 132.3 (C3); 138.7 (Cи); 146...); 123.9 (CмA); 126.7 (CoA); 127.8 (C5); 128.0, 129.1 (Co,мB); 128...); 123.9 (Cм); 125.4 (Co); 126.6 (C5); 131.9 (C3); 138.8 (Cи); 146...); 129.1 (CоA); 130.7 (CоB); 133.0 (C5); 140.3 (CиA); 141.6 (CиB); 147....9, 130.0 (3 CHAr); 132.2 (CиB); 134.7 (C5); 137.9 (CпB); 140.8 (CиA); 147....7, 130.0 (3 CHAr); 131.5 (CпB); 132.0 (C5); 136.2 (CиB); 140.9 (CиA); 147... 129.5 (CоB); 130.6 (CоA); 131.7 (C5); 133.5 (CиB); 140.8 (CиA); 141....4 (CиB); 129.7, 130.5 (CоA,B); 131.2 (C5); 140.9 (CиA); 146.9 (C4); 147....6, 130.5 (3 CHAr); 132.1 (CиA); 133.3 (C5); 133.9 (CпA); 141.6 (CиB); 146...); 131.1 (CпB); 132.7(CиA); 133.0 (C5); 135.2 (CпA); 136.5 (CиB); 147....4, 130.3 (4 CHAr); 132.7(CиA); 132.9 (C5); 133.8 (CиB); 135.1 (CпA); 141...); 129.2 (CиB); 132.2(CиA); 132.9 (C5); 135.0 (CпA); 147.1 (C4); 157....2 (3 CHAr); 129.3 (CпA); 133.7 (C5); 135.2 (CиA); 142.4 (CиB); 147.5 (C4); 149... ); 128.9 (CпA); 134.2, 134,3 (CиA, C5); 135.2 (CиB); 137.3 (CпB); 147...); 131.0 (CпB); 134.1, 134.3 (CиA, C5); 136.7 (CиB); 147.3 (C4); 157...); 128.8 (CпA); 133.8, 134.0 (CиB, C5); 134.4 (CиA); 141.3 (CпB); 147....7 (CпA); 109 129.3 (CиB); 133.4 (C5); 134.5 (CиA); 147.1 (C4); 157... 129.2 (3 CHAr); 130.5 (CиA); 134.6 (C5); 138.8 (CпA); 141.9 (CиB); 146....4, 129.6 (4 CHAr); 131.2 (CиA); 134.3 (C5); 135.2 (CиB); 137.2 (CпB); 139...); 130.9 (CпB); 131.3 (CиA); 134.1 (C5); 136.7 (CиB); 138.9 (CпA); 147...); 131.5 (CиA); 133.8 (CиB); 134.1 (C5); 138.8 (CпA); 141.3 (CпB); 147...); 129.4 (CиB); 131.5 (CиA); 133.3 (C5); 138.8 (CпA); 147.0 (C4); 157....9, 130.5 (3 CHAr); 125.5 (CиA); 134.4 (C5); 142.1 (CиB); 146.7 (C4); 149.0 (CпB... 128.3, 129.0, 129.9 (3 CHAr); 133.3 (C5); 135.0 (CиB); 135.6 (CпB); 146....6, 130.2 (3 CHAr); 130.9 (CпB); 133.8 (C5); 136.7 (CиB); 146.9 (C4); 157....1, 130.0 (3 CHAr); 133.3(CиB); 133.8 (C5); 140.9 (CпB); 146.7 (C4); 157....4 (CиB); 129.9, 130.2 (CоA,B); 133.0 (C5); 146.8 (C4); 157.4 (C6); 160....7, 130.1 (3 CHAr); 131.4 (CпB); 131.7 (C5); 136.4 (CиB); 141.3 (CиA); 147...); 129.1 (CоB); 130.8 (CпB); 134.0 (C5); 134.6 (CиA); 136.9 (CиB); 147....5, 130.4 (3 CHAr); 130.7 (CпB); 133.6 (C5); 136.9 (CиB); 147.5 (C4); 157...); 145.1, 146.8 (C2, CпA); 153.9 (C5); 159.3 (CпB); 184.0 (C3) м.д. Масс...); 145.2, 145.9 (C2, CпA); 153.5 (C5); 184.1 (C3) м.д. Масс-спектр (ЭСИ...); 145.3, 146.2 (CпA, C2); 153.4 (C5); 161.9 (д, JC-F = 249.2 Гц, CпB...); 144.5, 144.6 (C2, CпA); 156.6 (C5); 165.5 (COO); 183.9 (C3) м.д. Масс...); 145.0, 145.6 (C2, CпA); 152.5 (C5); 184.1 (C3) м.д. Масс-спектр (ЭСИ...); 146.1 (Cп); 149.0 (C2); 157.4 (C5); 184.8 (C3) м.д. Масс-спектр (ЭСИ...’); 146.3, 146.4 (C2, Cп); 156.4 (C5); 184.8 (C3) м.д. Масс-спектр (ЭСИ...); 113.7 (C3’); 121.4, 121.9 (=CSi, C5’); 124.6, 124.9 (Cо,м); 126.6 (C1....7, 147.4 (C2, Cп); 156.0, 158.2 (C5, C2’); 184.8 (C3) м.д. Масс-спектр...); 145.7, 146.9 (C2, CпA); 158.0 (C5); 184.5 (C3) м.д. Масс-спектр (ЭСИ....2 (Cи,пA, CоB, C2); 158.2 (C5); 184.5 (C3) м.д. Масс-спектр (ЭСИ....8 (C5’); 123.8 (Cм); 125.6 (=CSi); 125.7 (Cо); 137.4 (Cи); 139.4 (C4’); 142.3, 145.3 (C2, Cп); 153.5 (C5); 158.5 (C2’); 183....9 (CпA, C2); 150.9 (C3’); 151.9 (C5); 183.4 (C3) м.д. Масс-спектр (ЭСИ...); 145.2, 147.1 (Cп, C2); 158.1 (C5); 184.9 (C3) м.д. Масс-спектр (ЭСИ...); 145.2, 147.7 (Cп, C2); 154.8 (C5); 185.1 (C3) м.д. Масс-спектр (ЭСИ...); 145.2, 146.0 (C2, Cп); 156.8 (C5); 185.0 (C3) м.д. Масс-спектр (ЭСИ...); 145.5, 147.1 (C2, CпA); 158.2 (C5); 185.0 (C3) м.д. Масс-спектр (ЭСИ....7 (Cп, C2); 150.2 (C2’); 157.6 (C5); 184.9 (C3) м.д. Масс-спектр (ЭСИ...); 144.3, 145.4 (CпA, C2); 157.1 (C5); 183.8 (C3) м.д. Масс-спектр (ЭСИ...); 131.6 (Cи); 146.9 (C2); 152.7 (C5); 158.7 (CпB); 185.0 (C3) м.д. Масс...); 138.6 (CиB); 146.2 (C2); 152.4 (C5); 185.3 (C3) м.д. Масс-спектр (ЭСИ...); 131.4 (CиB); 146.9 (C2); 151.9 (C5); 158.0, 158.6 (2 Cp); 185.2 (C3...); 138.6 (CиB); 146.0 (C2); 151.3 (C5); 158.1 (CпA); 185.3 (C3) м.д. Масс...); 147.9, 149.2 (C2, CпA); 148.4 (C5); 157.5 (C3a) м.д. Массспектр (ЭСИ), m/z: вычислено...); 147.7, 149.0 (C2, CпA); 148.3 (C5); 157.2 (C3a) м.д. Масс-спектр (ЭСИ...); 148.0, 149.2 (C2, CпA); 148.7 (C5); 156.1 (C3a) м.д. Масс-спектр (ЭСИ... indenes via Au(I)-catalyzed C1-C5 cyclization of enediynes bearing an.... Catal. – 2011. – Vol. 353. – P. 3640. 142. Liu, R. Palladium(II)-Catalyzed Stereospecific... 8.4. Спектр 2D NOESY соединения 33b 142 8.5. Спектр 2D NOESY соединения 34b...



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0.19/5
....9 (CH3-C8) 126.7 (C1) 133.2 (C5) 142.6 (C2) 144.1 (C6) 122.9, 123....67 139.6 (C8a) 141.5 (C7a) 142.0 (C4a) 2.5.2 ESR Study: The products....9, 123.0 (C4,8) 126.7 (C1) 133.2 (C5) 135.1 (C3a) 139.6 (C8a) 141... of Polyalkylated 1,5-dihydro-s-Indacene Ligands 142.0 (C4a) 142.6 (C2) 144.1 (C6) Mass....36 148.54 115.37 C5 124.38 124.19 145... 1 116.48 JC-Rh = 1.1 Hz C5,7 1 71.81 JC-Rh = 4.9 Hz...(3) C3a-C4 C4-C4a C4a-C5 C5-C6 C6-C7 C7-C7a...)] 2 2 ΔRh2-C= {(Rh − C 7 a) + ( Rh − C 4a) {(Rh − C5) + (Rh − C7)] 2 2 3.6.4.3 X-ray Structure of...], much shorter than bonds C4a-C5, C7a-C7, C3a-C4 and... C1-C8a C1-C2 C4a-C5 C6-C7 C4-C4a C3a...(16) 14.0º Ru-C4a Ru-C5 Ru-C6 Ru-C7 Ru...-C7a C3-C3a C2-C3 C5-C6 C7-C7a C7a-C8...-C27 2.172(13) 2.136(12) 2.142(11) Ru-C24 Ru-C26... − C3)] 2 2 {(Rh − C 7 a) + ( Rh − C 4a) {(Rh − C5) + (Rh − C7)] ΔRh-C= 2 2 ΔRu-C= Cg1.... Melting Point: 1 H-NMR (C6D6, δ ppm): 142-147°C 0.62 (t, 2H, CH2, 3JH...%) Melting Point: 1 H-NMR (CDCl3, δ ppm): 142-144°C 1.65-1.88 (m, 8H, CH2... = 5.2 Hz) 113.2 (C3a,7a) 119.4 (C5,6) 122.7 (C4,7) 103 Rh-NMR...,7a, 1JC-Rh = 1.4 Hz) 120.1 (C5,6) 121.6 (C4,7) 103 Rh-NMR...,7a, 1JC-Rh = 1.6 Hz) 118.8 (C5,6) 125.1 (C4,7) 190.1 (CO) 132... (bs, 2H, C1,3-H) 6.60 (s, 1H, C5-H) 13 C-NMR (C6D6, δ ppm): 9.69...) 119.60 (C4) 124.19 (C5) 125.39 (C7a) 135.20... (br. s, 2H, C1,3-H) 6.24 (s, 1H, C5-H) 13 C-NMR (C6D6, δ ppm): 10...) 123.52 (C8) 124.38 (C5) 134.13 (C7a) 135 Chapter..., C1,3-H, 4JRh-H = 1.6 Hz) 6.67 (s, 1H, C5-H) 13 C-NMR (C6D6, δ ppm): 13...) 119.56 (C7a) 124.84 (C5) 136.23 (C8) 139.57... (br.s, 2H, C1,3-H) 6.74 (s, 1H, C5-H) 13 C-NMR (CD3CN, δ ppm): 8.75...) 144.62 (C7a) 145.38 (C5) 148.39 (C8) 148.54..., 3JH-H = 7.5 Hz, 3JH-Rh = 1.4 Hz) 142 Chapter 3: Synthesis and Spectroscopic Study...) 4.20 (s, 2H, C1,3-H) 5.04 (s, 2H, C5,7-H) 13 C-NMR (C6D6, δ ppm): 10...-Rh = 13.0 Hz) 71.81 (d, C5,7, 1JC-Rh = 4.9 Hz) 77.01...) 4.74 (s, 2H, C1,3-H) 5.00 (s, 2H, C5,7-H) 13 C-NMR (C6D6, δ ppm): 10...-Rh = 13.1 Hz) 71.73 (d, C5,7, 1JC-Rh = 4.5 Hz) 81.71...) 4.61 (s, 2H, C1,3-H) 4.90 (s, 2H, C5,7-H) 13 C-NMR (C6D6, δ ppm): 11...-Rh = 10.3 Hz) 72.71 (d, C5,7, 1JC-Rh = 5.1 Hz) 147 Chapter...) 5.38 (s, 2H, C1,3-H) 5.53 (s, 2H, C5,7-H) 13 C-NMR (CD3CN, δ ppm): 14....30 (CH2-COD) 69.68 (C5,7) 74.51 (d, C=C, COD, 1JC-Rh...



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0.3/5
... of Belgrade, 5 Bulevar despota Stefana 142, 11000 Belgrade and Institute of...}”, Univerzitet u Beogradu, Bulevar despota Stefana 142, 5 11000 Beograd i Institut za {umarstvo... the title compounds. 152.87 (C5), 141.95, 140.69, 140...): 154.54 (C3), 152.88 (C5), 141.65, 140.81, 140... (C=O), 153.72 (C3), 153.15 (C5), 142.14, 140.94, 135.20... (C=O), 153.92 (C3), 153.24 (C5), 141.94, 141.15, 141...), 153.20 (C3), 153.00 (C5), 142.13, 140.88, 140.43...), 152.99 (C3), 152.84 (C5), 141.65, 141.25, 140... 1,2,4-TRIAZOLES 1047 The C3 and C5 heterocyclic carbons from the new... 131.23s 135.90s138.33s 142.64s 47.48s [Ru(CO....20s 135.91s 138.34s 142.6s 47.90s (–0.03) (–0.06....56 127.59t 135.88s 142.76s 153.65s 47.12s... 132.06d 131.14s139.03s 142.54s 46.14s L6 [Ru....18s 130.66s 139.02s 142.36s 47.15s (–4.43) (–5.88... on a reversed phase Clean-up® C5 cartridge was developed. In the... with a reversed phase Clean-up® C5 cartridge. The complex was eluted... on a reversed phase Clean-up® C5 cartridge is described. Based on... using a reversed phase Clean-up® C5 cartridge (Unitie Chemical Technologies Corporation... was passed through a Clean-up® C5 cartridge at a flow rate of... phosphoric acid medium, a Clean-up® C5 cartridge was used. Both enrichment... medium. 0.10 g of Clean-up® C5, C8, C10, C12 and C18...-up® cartridges Adsorption capacity, mmol/g C5 0.254 C8 0.203 C10 0.178... C18 0.107 The Clean-up® C5 cartridge was found to have...). It appears that Clean-up® C5 is the most appropriate sorbent... SOLID PHASE EXTRACTION 1141 -up® C5 cartridge is applied. The detection...јеног комплекса на Clean-up® C5 колони реверсних фаза. У присуству 0,02...



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0.04/5
..., LG, LM A29 A31 C44 C5 C21 LB A32 C22 C4.../14.61 x 161.93 PCD 142.88 82.55 76.20....63 C1 C2 C3 C4 C5 C6 C7 C10 C11 C12....17 94.45 114.30 142.83 169.95 50.80....30 242.75 34.93 142.09 61.91 104.86.../14.61 x 161.93 PCD 142.88 19.38/19.96... Class 5 fit A560 Class 6+ fit C5 B4 A34 B8 B1 B16... A22 C13 C20 TA, TJ C5 C26 C27 A24 QA, QJ... A9 117.48 146.05 142.88 A21 1/2 BSF 1/2 BSF 1/2 BSF....75 248.44 331.09 C5 142.09 134.61 154.77... B17 A6 A7 B4 B5 C5 C26 B7 A380 Port flange... Class 5 fit A560 Class 6+ fit C5 A9 RN, RS C6 16... B16 B17 C1 C2 C3 C5 C6 C7 C8 C9 C21....80 196.30 242.75 142.09 61.91 104.86.../14.61 x 161.93 PCD 142.88 30.16 62.12.../14.61 x 161.93 PCD 142.88 30.16 62.12... 47.63 C1 C2 C3 C5 C6 C11 C18 C19 C21....80 196.30 242.75 142.09 61.91 92.63...