REACTION OF SUBSTITUTED 7-CYCLOPROPYL-1,4-BENZODIOXANES WITH DINITROGEN TETRAOXIDE

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 three-membered 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.

Authors: S. S. Mochalov, R. A. Gazzaeva, V. N. Atanov, A. N. Fedotov, and N. S. Zefirov.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (3), pp 281-285

http://link.springer.com/article/10.1007/BF02259355