Behavior of propargyl- and allylpropargyl-ammonium salts in aqueous alkaline medium. Synthesis of 2-methyl-2-phenylbenz[<i>f</i>]isoindolinium and 2-methyl-2-phenylisoindolinium salts

Authors

  • Э. O. Чухаджян Institute of Organic Chemistry, Armenian Academy of Sciences, Erevan 375094
  • Л. А. Манаcян Institute of Organic Chemistry, Armenian Academy of Sciences, Erevan 375094
  • Эл. O. Чухаджян Institute of Organic Chemistry, Armenian Academy of Sciences, Erevan 375094
  • К. Г. Шахатуни Institute of Organic Chemistry, Armenian Academy of Sciences, Erevan 375094
  • А. T. Бабаян Institute of Organic Chemistry, Armenian Academy of Sciences, Erevan 375094

Abstract

Methylphenylpropargyl-(3-phenylpropargyl)ammonium bromide salts are cyclized almost quantitatively under base-catalysis conditions with the formation of 2-methyl-2-phenylbenz[f]isoindolinium bromide. The allyl analog is subject to rearrangement-decomposition, to a Stevens rearrangement, and to nucleophilic substitution, the cyclic product being obtained in low yield. Methylphenylpropargyl(3-vinylpropargyl)ammonium bromide is mainly cyclized, but the 3-isopropenylpropargyl analog of this salt is subject to cyclization and subsequent decomposition under analogous conditions.

Как ссылаться
Chukhadzhyan, É. O.; Manasyan, L. A.; Chukhadzhyan, Él. O.; Shakhatuni, K. G.; Babayan, A. T. Chem. Heterocycl. Compd. 1995, 31, 58. [Химия гетероцикл. соединений 1995, 68.]

Статья в английском издании журнала: DOI https://doi.org/10.1007/BF01171292

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Published

1995-01-25

Issue

No. 1 (1995)

Section

Original Papers