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Reaction of Me3CCMe(OH)CR:CH2 (I; R = H) with Br2 or NBS in aq. medium resulted in rearrangement, yielding ketones Me3CCOCHMeCH2Br and MeCOCR(CH2Br)CMe3 (III) and the oxirane II. With I (R = F, Me), bromination gave only ketone III. Competition expts. showed that I (R = F) underwent bromination at a much slower rate than I (R = H or Me). [on SciFinder (R)]
Albert Renken, Lioubov Kiwi, Philippe Buffat, Elena Suvorova Buffat