Галогенофильный механизм и классический механизм присоединения-элиминирования в реакциях нуклеофильного винильного замещения с участием анионов карбонилов переходных металлов
Lee S.J., Terrazas M.S., Pippel D.J., Beak P., Mechanism of Electrophilic Chlorination: Experimental Determination of a Geometrical Requirement for Chlorine Transfer by the Endocyclic Restriction Test. J. Am. Chem. Soc., 2003,125 (24), 73 077 312. Baciocchi E., Schiroli A., Dehalogenation Reactions of Vicinal Dihalides. Part II. Substituent and Leaving-group Effects in the Reactions of l… Читать ещё >
Галогенофильный механизм и классический механизм присоединения-элиминирования в реакциях нуклеофильного винильного замещения с участием анионов карбонилов переходных металлов (реферат, курсовая, диплом, контрольная)
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- ВЫВОДЫ
1. Исследованы реакции карбонилат-анионов ([М (СО)пЦ") с широким кругом винилгалогенидов, отличающихся как природой галогена (На1=Р, С1, Вг, 1), так и степенью активации двойной связи и пространственным строением реакционного центра. Изучен состав продуктов и кинетика реакций, показано, что реакции в большинстве случаев происходят с сохранением конфигурации двойной связи.
2. Найден необычный галогенофильный механизм нуклеофильного винильного замещения, первой стадией которого является нуклеофильная атака карбонилат-аниона по атому галогена. Образование продуктов замещения, обычных сг-винильных комплексов УтМ (СО)"Ь или гало (ацил)металлатов [Ут (СО)М (СО)4На1]" М=Ые, Мп, происходит в результате сочетания интермедиатов, винильного карбаниона и М (СО)пЬНа1. Строение гало (ацил)рената впервые охарактеризовано методом РСА.
3. Показано, что нуклеофильная атака карбонилата по атому галогена является общим явлением и выступает в качестве основной альтернативы классическому АёкЕ механизму нуклеофильного винильного замещения. Вероятность галогенофильной реакции увеличивается в ряду С1"Вг"1, большинство винилхлоридов и первичные винилбромиды реагируют по Ас1кЕ механизму. Решающую роль играет строение винилгалогенида: стабильность карбанионных интермедиатов Ас1иЕ или галогенофильной реакций и наличие пространственных препятствий для атаки нуклеофила по двойной связи. Галогенофильный механизм возможен даже в реакциях винилхлоридов с карбонилатами, также как механизм А<1мЕ возможен для винилиодидов.
4. Для сравнения изучены реакции тиолатов и карбанионов с теми же субстратами и показано, что они происходят по обычному АёкЕ механизму, что подтверждает более высокую «галогенофильность» металл-центрированных карбонилат-анионов по сравнению с С- и Б-нуклеофилами.
5. На примере реакций карбонилат-анионов впервые создана субстрат-независимая шкала нуклеофильности для реакций винильного замещения по Ас^Е механизму. Нуклеофильность карбонилатов хорошо коррелирует с их нуклеофильностью в алифатическом замещении, но изменяется в намного более широком диапазоне:
CpFe (CO)2]""[Re (CO)5]""[Mn (CO)5]">[CpW (CO)3]">[CpMo (CO)3]" *[M (C0)"L]M' ~1014 7−107 130 5 1
CpMo (CO)j]K
Расширенная шкала нуклеофильности карбонилатов справедлива и для галогенофильных реакций карбонилатов с винилгалогенидами.
6. Найдена корреляция lg (&on<) галогенофильных реакций с линейной комбинацией AEi реакции VinHal —> [Vin]" + Hal+ и АЕг реакции VinHal + [Мп (СО)5]~ —*¦ [Vin]- + Mn (CO)sHal, рассчитанных методом DFT.
7. Разработана модель, позволяющая предсказать скорость АёкЕ и галогенофильных реакций винилгалогенидов с карбонилатами, основанная на корреляции экспериментально полученных данных lg (A'0TII) с рядом параметров, рассчитанных методом DFT. Модель корректно предсказывает направление реакций винилгалогенидов с карбонилатами и позволяет построить ряд электрофильности винилгалогенидов в AcInE и галогенофильных реакциях.
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