Faculty Publications

Title

Bromonitrothiolene-1,1-dioxides in a 'halogen dance' reaction

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.

Original Publication Date

4-1-2004

DOI of published version

10.1080/17415990410001697123

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