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

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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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Authors and Affiliations

  1. Scientific and Technological Center of Organic and Pharmaceutical Chemistry, National Academy of Sciences of the Republic of Armenia, Institute of Organic Chemistry, pr. Azatutyana 26, Yerevan, 0014, Armenia

    E. O. Chukhajian, К. G. Shahkhatuni, El. O. Chukhajian, L. V. Ayrapetyan & G. A. Panosyan

Authors
  1. E. O. Chukhajian
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  2. К. G. Shahkhatuni
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  3. El. O. Chukhajian
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  4. L. V. Ayrapetyan
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  5. G. A. Panosyan
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Corresponding author

Correspondence to G. A. Panosyan.

Additional information

Original Russian Text © E.О. Chukhajian, К.G. Shahkhatuni, El.О. Chukhajian, L.V. Ayrapetyan, G.А. Panosyan, 2017, published in Zhurnal Organicheskoi Khimii, 2017, Vol. 53, No. 2, pp. 191–195.

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Chukhajian, E.O., Shahkhatuni, К.G., Chukhajian, E.O. et al. Deamination of 3-(dialkylamino)-1,4-diarylhex-5-en-1-ynes during vacuum distillation. Russ J Org Chem 53, 178–183 (2017). https://doi.org/10.1134/S1070428017020063

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  • DOI: https://doi.org/10.1134/S1070428017020063

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