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Reaction of substituted 7-cyclopropyl-1,4-benzodioxanes with dinitrogen tetraoxide

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The reaction of 6-bromo-7-cyclopropyl-1,4-benzodioxane with N2O4 in methylene chloride does not affect the cyclopropane ring and forms the nitrodebrominated product (ipso-substitution). The same reaction of 6-nitro- and 5,6-dinitro-7-cyclopropyl-1,4-benzodioxanes produces only the products with an modified threemembered ring. The difference in the reaction paths of the studied cyclopropylbenzodioxanes with N2O4 is explained by the different ratio of substrate to one-electron oxidant, the nitrosyl cation.

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M. V. Lomonosov Moscow State University, Moscow 119899

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 324–329, March, 1999.

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Mochalov, S.S., Gazzaeva, R.A., Atanov, V.N. et al. Reaction of substituted 7-cyclopropyl-1,4-benzodioxanes with dinitrogen tetraoxide. Chem Heterocycl Compd 35, 281–285 (1999). https://doi.org/10.1007/BF02259355

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  • DOI: https://doi.org/10.1007/BF02259355

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