- Deamination of 3-(dialkylamino)-1,4-diarylhex-5-en-1-ynes during vacuum distillation
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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.
- Chukhajian,Shahkhatuni,Chukhajian, El. O.,Ayrapetyan,Panosyan
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- Cyclization of dialkyl(3-phenylpropen-2-yl)-(3-phenylpropyn-2-l)ammonium bromides by the action of an aqueous alkali solution. aqueous-alkaline cleavage of the cyclization products - N,n-dialkyl-4(9)-phenyl-3a,4-dihydro-benzo[f] isoindolinium bromides
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When heated in an alkaline aqueous medium, dialkyl(3-phenylpropen-2-yl)(3- phenylpropyn-2-yl)- ammonium bromides undergo intramolecular cyclization, forming N,N-dialkyl-4(9)-phenyl-3a,4-dihydrobenzo[f]isoindolinium bromides. The cyclization products undergo aqueous-alkaline cleavage at the C(1)-N(2) or N(2)-C(3) bond, which leads to a mixture of 2-(dialkylaminomethyl)-3-methyl- and 3-(dialkylaminomethyl)-2-methyl-1-phenylnaphthalenes. However, only the C(1)-N(2) bond cleavage product is formed in the case of 2,2-pentamethylene-9- phenyl-3a,4-dihydrobenzo-[f]isoindolinium bromide.
- Chukhajian,Ayrapetyan,Chukhajian, El. O.,Panosyan
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p. 1314 - 1320
(2013/04/24)
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