An examination was made of some reactions involving a transfer
of carbon from boron to carbon. In the case of the reaction of
a C[subscript n] alkylorganoborane with dichlorocarbene the intermediate was
a C[subscript n]₊₁ chloroalkylorganoborane. Oxidation of this intermediate
yielded an homologous acid (33%) and the usual alcohol (66%)....
Steroid organoboranes have been found to be useful synthetic
intermediates. Attempted pyrolyses, based on simple trialkylborane
cyclizations, have not yielded C-19 or C-18 functionalized steroids,
but have produced isomerized systems not otherwise available.
Thus, hydroboration of cholesterol followed by pyrolysis at
215° gives 31% of 2-cholestene-6α-ol and 49% of a...