Bromohydrin formation in aqueous dimethyl sulphoxide; electronic and steric effects

DR Dalton, VP Dutta

Index: Dalton,D.R.; Dutta,V.P. Journal of the Chemical Society [Section] B: Physical Organic, 1971 , p. 85 - 89

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Citation Number: 17

Abstract

The role of electronic and steric effects in the stereospecific trans-addition of the elements of hypobromous acid (HOBr) to a selected group of olefins, with moist dimethyl sulphoxide as solvent-reactant and N-bromosuccinimide as the source of bromine, has been examined. In the absence of severe steric restrictions, the electronic effects have been observed to direct the addition in a Markownikoff sense. Highly hindered olefins and those wherein the ...