Sodium triethyl- (I) and triphenyl-trimethylsilylethynylborate (II), when treated with electrophilic reagents give (Z/E)-mixtures of tetrasubstituted alkenes III and IV. The influence of the trimethylsilyl group, incorporated in the borates I and II, on the stereoselectivity of the reaction was studied with the aid of 1H and 11B nmr. A novel rearrangement of bis-trimethylsilylalkenes IIId and IVd was also investigated.
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Hagelee et al. (1977) studied this question.
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