Deamination of 3-(dialkylamino)-1,4-diarylhex-5-en-1-ynes during vacuum distillation |
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Authors: | E O Chukhajian К G Shahkhatuni El O Chukhajian L V Ayrapetyan G A Panosyan |
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Institution: | 1.Scientific and Technological Center of Organic and Pharmaceutical Chemistry,National Academy of Sciences of the Republic of Armenia, Institute of Organic Chemistry,Yerevan,Armenia |
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Abstract: | 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. |
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