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Dichloromethane as solvent and reagent: a case study of photoinduced reactions in mixed phosphonium‐iodonium ylideстатья
Информация о цитировании статьи получена из
Web of Science,
Scopus
Статья опубликована в журнале из списка Web of Science и/или Scopus
Дата последнего поиска статьи во внешних источниках: 10 августа 2018 г.
- Авторы: Levina I.I., Klimovich O.N., Vinogradov D.S., Podrugina T.A., Bormotov D.S., Kononikhin A.S., Dement'eva O.V., Senchikhin I.N., Nikolaev E.N., Kuzmin V.A., Nekipelova T.D.
- Журнал: Journal of Physical Organic Chemistry
- Том: 31
- Номер: 7
- Год издания: 2018
- Издательство: John Wiley & Sons Inc.
- Местоположение издательства: United States
- Первая страница: e3844
- DOI: 10.1002/poc.3844
- Аннотация: Several years ago the photoinduced reaction of mixed phosphonium‐iodonium ylides (1) with acetylenes (2) to give λ5‐phosphinolines (3) and substituted furans (4) was described. This reaction is one‐pot, metal‐free synthesis of heterocycles 3 and 4 with the yields of 40% to 80%. The reaction proceeds only in dichloromethane (DCM) at the high ylide concentrations (>0.01 mol/L). The product analysis by 31P NMR, electrospray ionization mass spectrometry, UVvis spectrophotometry, and the dynamic light scattering study of the self‐aggregation of the ylide in DCM showed a dual role of the solvent in the photoinduced reactions of mixed phosphonium‐iodonium ylide: (i) at the low ylide concentrations (<0.01 mol/L), the conjugated photoinitiation of the chain reaction in DCM results in the formation of chlorine‐containing products and (ii) at the high ylide concentrations (>0.01 mol/L), the photolysis mechanism is determined by self‐organization of the ylide molecules to give large stable aggregates in DCM, in which the target heterocycles are synthesized. Two important issues follow from the study. First, the annulation reaction between mixed phosphonium‐ iodonium ylide and acetylenes occurs only when the reactive intermediates are in close proximity to one other, and, second, DCM is not inert reagent in reactions occurring with participation of radicals and in one form or another can participate in photoinduced radical reactions of various solutes.
- Добавил в систему: Дементьева Ольга Вадимовна