Deamination of 3-(dialkylamino)-1,4-diarylhex-5-en-1-ynes during vacuum distillation


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Resumo

During vacuum distillation of 3-(dialkylamino) derivatives of 1,4-diphenyl- and 4-phenyl-1-(p-chlorophenyl) hex-5-en-1-ynes deamination occurs resulting in a high yield of p-diarylbenzenes. The amines transformation into terbenzenes is a domino-reaction: first step consists in the β-elimination of secondary amines with the generation of conjugated dienyne which via an electrocyclic reaction transforms into cyclic allene intermediate. The latter after 1,3- or 1,5-hydride shift quickly converts into the final reaction products.

Sobre autores

E. Chukhajian

Scientific and Technological Center of Organic and Pharmaceutical Chemistry

Email: qnarsh@yandex.ru
Armênia, pr. Azatutyana 26, Yerevan, 0014

К. Shahkhatuni

Scientific and Technological Center of Organic and Pharmaceutical Chemistry

Email: qnarsh@yandex.ru
Armênia, pr. Azatutyana 26, Yerevan, 0014

El. Chukhajian

Scientific and Technological Center of Organic and Pharmaceutical Chemistry

Email: qnarsh@yandex.ru
Armênia, pr. Azatutyana 26, Yerevan, 0014

L. Ayrapetyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry

Email: qnarsh@yandex.ru
Armênia, pr. Azatutyana 26, Yerevan, 0014

G. Panosyan

Scientific and Technological Center of Organic and Pharmaceutical Chemistry

Autor responsável pela correspondência
Email: qnarsh@yandex.ru
Armênia, pr. Azatutyana 26, Yerevan, 0014

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