Changing behavior: A nucleophilic sp2 carbene-type boryl moiety, formed upon interaction of tetraalkoxydiboranes and a Lewis base, can attack non-activated CC bonds. Computational studies identify the interaction as the overlap between the strongly polarized BB σ bond (HOMO) and the antibonding π* orbital (LUMO) of the CC bond. Conceptually, the normally electrophilic boron becomes nucleophilic and forces the olefin to act as an electrophile.
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Bonet et al. (2011) studied this question.
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