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Intramolecular cyclization ofgem-benzylaminoallylcyclohexane under the action of sulfuric acid

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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].

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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.

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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

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  • Alcohol
  • Organic Chemistry
  • Chloroform
  • Sulfuric Acid
  • Boiling