Why is the following interconversion slowest for crotyl boronates and fastest for crotyl boranes while crotyl borinates are somewhere in-between?
4
$\begingroup$
$\endgroup$
6
$\begingroup$
$\endgroup$
The lack of an octet and the empty p-orbital on boron make trialkyl boron compounds quite reactive. If we replace one of the alkyl ligands with an alkoxy group (borinate), we can now draw a resonance structure where oxygen shares one of its lone pairs with boron. In such a resonance structure the boron atom has achieved an octet and the empty p-orbital on boron has been filled. Consequently borinates are less reactive than the corresponding boranes. Boronates, with two alkoxy substituents, have an even higher contribution from the resonance structure with the $\ce{B^{-}=O^+}$ double bond and are even less reactive.
