Abstract
Perfluoroalkylmagnesium bromide, C n F 2 n+1 MgBr ( n = 2, 6, 8), reacts with α,β-unsaturated aldehydes to give allylic alcohols as the sole products. No attack on the β-carbon atom of the carbonyl was detected, even when the reaction was carried out in the presence of CuCl. Part of the Grignard reagent decomposes to trans-R FCFCFBr and trans-R FCFCFI. Neither a mechanism involving dissociation into R + F MgX - nor the formation of a carbene intermediate is capable of explaining the thermal decomposition of the Grignard reagent.
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