Grignard reagents reaction with bromohydrins

The characteristic ease with which ethylene oxides undi ruu nucleophilic attack or isomerization in tbe presence of Lewie acids made them obvious substrates for tbe org nometallic reagents intro duoed by Grignard 07 around the turn of the century, and subsequently named in his hunor. The earliest disclosure of a reaction between an epoxide and a Grignard reagent, however, bears the name of Blaise,1 who noted the formation of ethylene bromohydrin on troii merit of ethylene oxide with raethylmagneeium bromide. In the years... 

The reaction of phenylmagnesium bromide with 1,3,2-dioxathioIane 2-oxide (16) gave 3.4-23% ethylene bromohydrin (131) and 42-60% diphenyl sulfoxide (132), depending on the conditions of the reaction. The bromohydrin (131) arises from a nucleophilic displacement at carbon by bromide ion, presumably via (129) and (130), while the sulfoxide (132) is formed by repeated attack of the Grignard reagent at sulfur (56JA454). 

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