Base catalyzed intramolecular cyclization of dialkycrotyl(3-alkenylpropyn-2-yl)ammonium salts and aqueous base fission of 2,2-dialkyl-4-methyl-and 2,2-dialkyl-4,6-dimethyl-2,6,7,7a-tetrahydro-1H-isoindolium bromides |
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| Authors: | E. O. Chukhajian M. K. Nalbandyan A. R. Gevorkyan K. G. Shakhatuni G. A. Panosyan |
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| Affiliation: | (1) Institute of Organic Chemistry, National Academy of Sciences of the Republic of Armenia, Yerevan, 375091, Armenia;(2) Molecular Structure Research Center, National Academy of Sciences of the Republic of Armenia, Yerevan, 375014, Armenia |
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| Abstract: | Cyclization of dimethylcrotyl(3-vinyl-or-3-isopropenylpropyn-2-yl)ammonium bromides in the presence of base gave a mixture of the isomeric 2,2-dialkyl-4-methyl-and 2,2-dialkyl-4,6-dimethyl-2,6,7,7a-tetrahydro-1H-isoindolium bromides. Basic fission of the salts obtained at increased temperature gave a mixture of the isomeric N,N-disubstituted di-and trimethylbenzylamines whose structures were confirmed by their IR, 1H NMR, and 13C NMR spectra. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 841–846, June, 2008. |
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| Keywords: | 2,2-dialkyl-4-methyl-and-4,6-dimethyl-2,6,7,7a-tetrahydro-1H-isoindolium bromides isomeric N, N-dialkylmethyl-and-trimethylbenzylamines intramolecular cyclization aqueous base fission basic catalysis |
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