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

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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.

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References

  1. É. O. Chukhadzhyan, A. V. Atomyan, N. T. Gevorkyan, É. O. Chukhadzhyan, F. S. Kinoyan, and A. T. Babayan, Khim. Geterotsikl. Soedin., No. 1, 63 (1995).

  2. A. T. Babayan, É. O. Chukhadzhyan, and G. T. Babayan, Zh. Org. Khim.,6, 1161 (1970).

    Google Scholar 

  3. A. T. Babayan, É. O. Chukhadzhyan, and É. O. Chukhadzhyan, and F. S. Kinoyan, Arm. Khim. Zh.,23, 150 (1970).

    Google Scholar 

  4. É. O. Chukhadzhyan, É. O. Chukhadzhyan, and A. T. Babayan, Zh. Org. Khim.,10, 46 (1974).

    Google Scholar 

  5. É. O. Chukhadzhyan, G. L. Gabrielyan, and A. T. Babayan, Zh. Org. Khim.,11, 325 (1975).

    Google Scholar 

  6. L. A. Kazitsyna and N. B. Kupletskaya, Application of UV, IR, NMR, and Mass Spectroscopy in Organic Chemistry [in Russian], Izv-vo MGU, Moscow (1979), pp. 33.

    Google Scholar 

  7. V. Braun, A. Fussgänger, and J. Kühn, Justus Liebigs Ann. Chem.,445, 206 (1925).

    Google Scholar 

  8. V. Braun, Chem. Ber.,33, 2733 (1900).

    Google Scholar 

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Authors and Affiliations

  1. Academy of Sciences of the Armenian Republic, Institute of Organic Chemistry, 375094, Yerevan

    É. O. Chukhadzhyan, L. A. Manasyan, Él. O. Chukhadzhyan, K. G. Shakhatuni & A. T. Babayan

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  1. É. O. Chukhadzhyan
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  2. L. A. Manasyan
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  3. Él. O. Chukhadzhyan
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  4. K. G. Shakhatuni
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  5. A. T. Babayan
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Additional information

Part 225 of the series on “Investigations on Amines and Ammonium Compounds,” see [1] for part 224.

Deceased

Translated from Khimiya Geterotsklicheskikh Soedinenii, No. 1, pp. 68–72, January, 1995.

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Chukhadzhyan, É.O., Manasyan, L.A., Chukhadzhyan, É.O. et al. Behavior of propargyl- and allylpropargyl-ammonium salts in aqueous alkaline medium. Synthesis of 2-methyl-2-phenylbenz[f]isoindolinium and 2-methyl-2-phenylisoindolinium salts. Chem Heterocycl Compd 31, 58–62 (1995). https://doi.org/10.1007/BF01171292

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  • DOI: https://doi.org/10.1007/BF01171292

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