Alkylation and Allylation of Lithium Arylborates Factors Affecting the Di/Mono Substitution Ratio $^\dag$

Alkylation and allylation of arylborates give mono(ipso) and/or di(ortho and ipso) substitution products. Those factors which promote polarization or ionization of alkylating agents favor di substitution. The -type(ipso) substitution reaction of arylborates involves direct interaction of the carbon-boron bonds rather than predissociation of arylborates into aryllithiums and boranes.