Bromonitrothiolene-1,1-Dioxides In A 'Halogen Dance' Reaction

Authors

I. E. Efremova, Herzen State Pedagogical University of RussiaFollow
V. V. Abzianidze, Herzen State Pedagogical University of RussiaFollow
J. E. Elbert, University of Northern IowaFollow
V. M. Berestovitskaya, Herzen State Pedagogical University of RussiaFollow

Document Type

Article

Keywords

Bromotropic rearrangement, Halogen dance, Halogen migration, Heterocycles, Mono- and dibromonitrothiolene-1, 1-dioxides, Prototropic rearrangement, Thiolene-1, 1-dioxides (dihydrothiophene-1, 1-dioxides)

Journal/Book/Conference Title

Journal of Sulfur Chemistry

Volume

25

Issue

2-3

First Page

89

Last Page

94

Abstract

The chemical behavior of 4-bromo-3-methyl-4-nitro-2- and 2-bromo-3-methyl-4-nitro-3-thiolene-1,1-dioxides in different solvents has been studied. These dioxides can undergo halo- and prototropic rearrangements, simultaneously in polar solvents, under very mild conditions. These transformations lead to another isomer, 2-bromo-3-methyl-4-nitro-2-thiolene-1, 1-dioxide and products of disproportionation, such as 2,4-dibromo-3-methyl-4- nitro-2-thiolene-1,1-dioxide and δ2- and δ3- nitrothiolene dioxides.

Department

Department of Chemistry

Original Publication Date

4-1-2004

DOI of published version

10.1080/17415990410001697123

Recommended Citation

Efremova, I. E.; Abzianidze, V. V.; Elbert, J. E.; and Berestovitskaya, V. M., "Bromonitrothiolene-1,1-Dioxides In A 'Halogen Dance' Reaction" (2004). Faculty Publications. 3121.
https://scholarworks.uni.edu/facpub/3121