Abstract
When treated with 855 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].
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
V. V. Kuznetsov, S. V. Lantsetov, A. E. Aliev, A. V. Varlamov, and N. S. Prostakov, Zh. Org. Khim.,28, 74 (1992).
G. A. Dilbeck, L. Don Morris, and K. D. Berlin, J. Org. Chem.,40, 1150 (1975).
S. D. Venkataramu, G. D. Macdonell, W. R. Purdum, G. A. Dilbeck, and K. D. Berlin, J. Org. Chem.,42, 2195 (1977).
Additional information
Russian University of International Friendship, Moscow 117198. School of Chemistry, Industrial University of Santander, Bucaramanga, A. A. 678, Colombia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 223–227, February, 1999.
Rights and permissions
About this article
Cite this article
Varlamov, A.V., Zubkov, F.I., Chernyshev, A.I. et al. Intramolecular cyclization ofgem-benzylaminoallylcyclohexane under the action of sulfuric acid. Chem Heterocycl Compd 35, 199–203 (1999). https://doi.org/10.1007/BF02251709
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02251709