Trialkylcarbinols, from trialkylboranes

Numerous other reactions include the synthesis of trialkylcarbinols from trialkylboranes (Brown, H. C. Acc. Chem. Res. 1969, 2, 65) and hydroboration-protonolysis leading to alkanes (Brown, H. C. Murray, K. /. Am. Chem. Soc. 1959,81,4108). Isomerization and disproportionation of the alkylboranes was also seen (reference 230b). 

Triaikykarbinols from trialkylboranes. Trialkylcarbinols have been prepared by the reaction of trialkylboranes with carbon monoxide in diglyme followed by oxidation with hydrogen peroxide (equation 1). See 2, 60. The method has the disadvantage that at the temperature required isomerization of organoboranes can be significant. 

Preparation.—Variations continue to appear on the theme of alcohol production by hydroboration-oxidation of olefins. 5-Methoxydialkylboranes react with olefins in the presence of lithium aluminium hydride to afford a new route to trialkylboranes and thence, by carbonylation-oxidation, to trialkylcarbinols. Carbonylation with carbon monoxide is avoided in a new procedure in the presence of an excess of trifluoroacetic anhydride, trialkyl cyanoborates undergo a triple alkyl migration from boron to carbon to give, on oxidation, high yields of trialkylcarbinols (Scheme 126). Tri-... 

---