Bromonitrothiolene-1,1-dioxides in a 'halogen dance' reaction
Bromotropic rearrangement, Halogen dance, Halogen migration, Heterocycles, Mono- and dibromonitrothiolene-1, 1-dioxides, Prototropic rearrangement, Thiolene-1, 1-dioxides (dihydrothiophene-1, 1-dioxides)
Journal of Sulfur Chemistry
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
DOI of published version
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.