The nature of the borane-olefin interactions that take place prior to frustrated Lewis pair addition reactions has been probed employing a Lewis acidic borane tethered to a vinyl group through an alkyl chain. (1)H{(19)F} HOESY spectral data obtained at -50 °C demonstrated the spatial proximity of the boryl and vinyl groups and computational data support the initial formation of a van der Waals borane-olefin complex. Such species serve as intermediates undergoing facile addition reactions with phosphine bases to afford cyclic zwitterionic products.
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Zhao et al. (2011) studied this question.