INTRAMOLECULAR CYCLIZATION OF <i>gem</i>-BENZYLAMINOALLYLCYCLOHEXANE UNDER THE ACTION OF SULFURIC ACID

Authors

  • А. B. Варлaмов Russian University of International Friendship
  • Ф. И. Зубков Russian University of International Friendship
  • А. И. Чернышев Russian University of International Friendship
  • B. В. Кузнецов Russian University of International Friendship
  • А. P. Пальма School of Chemistry, Industrial University of Santander

DOI:

https://doi.org/10.1007/533

Abstract

When treated with 85% sulfuric acid at 85°C, gem-benzylaminoallylcyclohexane is converted to spiro[tetrahydrobenz-2-azepine-3-cyclohexane], while at 20°C or in boiling chloroform 3,4,5,6-tetrahydro-3-benzyl-6-methylspiro[1,2,3-oxathiazine-2,2-dioxide-4-cyclohexane] is formed as the major product. The second compound is cleaved by alcohol solution of alkali to 1-benzyl-4-methylspiro[azetidine-2-cyclohexane].

Authors: A. V. Varlamov, F. I. Zubkov, A. I. Chernyshev, V. V. Kuznetsov, and A. R. Palma.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (2), pp 199-203

http://link.springer.com/article/10.1007/BF02251709

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Published

2013-04-26

Issue

No. 2 (1999)

Section

Original Papers