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Intramolecular cyclization ofgem-benzylaminoallylcyclohexane under the action of sulfuric acid

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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].

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References

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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.

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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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Keywords

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