Dalton, David R. published the artcileBromohydrin formation in aqueous dimethyl sulphoxide; electronic and steric effects, Application In Synthesis of 2588-77-4, the publication is Journal of the Chemical Society [Section] B: Physical Organic (1971), 85-9, database is CAplus.
The role of electronic and steric effects in the stereospecific trans-addition of HOBr to olefins, with moist Me2SO as solvent-reactant and N-bromosuccinimide as the source of Br, was examined In the absence of severe steric restrictions, the electronic effects were observed to direct the addition in a Markovnikov sense. Highly hindered olefins and those wherein the electron d. at the C:C double bond is severely depleted by electron-withdrawing substituents fail to react. Similar systems which have shown a susceptibility to carbonium ion rearrangements in analogous reactions fail to yield, for the most part, rearranged products. The intermediate is deemed best represented by a bromonium ion, symmetrical or nonsymmetrical, depending upon the structure of the starting olefin. If the addition of HOBr is retarded owing to electronic or steric effects, considerable amounts of dibromide accompany bromohydrin.
Journal of the Chemical Society [Section] B: Physical Organic published new progress about 2588-77-4. 2588-77-4 belongs to alcohols-buliding-blocks, auxiliary class Aliphatic Chain, name is 2-Methyl-3-bromo-2-butanol, and the molecular formula is C5H11BrO, Application In Synthesis of 2588-77-4.
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