Behavior of 6-cyclopropyl- and 6-bromo-7-cyclopropyl-1,4-benzodioxanes under electrophilic substitution reaction conditions

Abstract

Bromination of 6-cyclopropyl-1,4-benzodioxane occurs with concerted orientation of the ethylenedioxy group and the cyclopropyl radical for the least sterically hindered position of the aromatic ring. Nitration of 6-bromo-7-cyclopropyl-1,4-benzodioxane does not lead to products of substitution of the hydrogen atom in the 5 or 8 position of the 1,4-benzodioxane, but rather to the nitrodebromination product: 7-nitro-6-cyclopropyl-1,4-benzodioxane. The anomalous behavior of the bromo-substituted benzodioxane is explained by the predisposition of the carbon atom bonded to the bromine toward ipso attack by an electrophile.

How to Cite
Mochalov, S. S.; Atanov, V. N.; Zefirov, N. S. Chem. Heterocycl. Compd. 1998, 34, 542. [Khim. Geterotsikl. Soedin. 1998, 34, 618.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF02290935