B-l-Alkenyl-9-borabicyclo 3.3.1 nonanes

B-l-Alkenyl-9-borabicyclo[3.3.1]nonanes (1). These substances are prepared by hydroboration of alkynes with 9-BBN (2, 31 3, 24-29 4, 41 5, 46-47 6, 62-64). -Allylic alcohols. Usually reaction of organoboranes with carbonyl groups results in reduction. However, B-l-alkenyl-9-borabicyclo[3.3.1.]nonanes (1) add to simple aldehydes to give, after oxidation, allylic alcohols, with retention of configuration (equation I). The reaction is a Grignard-like synthesis and should be a useful route to allylic alcohols, even to those containing functional groups. 

ALLYLIC ALCOHOLS B-l-Alkenyl-9-borabicyclo[3.3.1 nonanes. Benzene-selenenic acid. Borane-Dimethyl sulfide. 

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