Hydroboration kinetics: Unusual kinetics for the reaction of 9-borabicyclo[3.3.1]nonane with representative alkenes*

AUTOR(ES)

Brown, Herbert C.

RESUMO

The kinetics of hydroboration of alkenes with 9-borabicyclo[3.3.1]nonane dimer, (9-BBN)2, exhibit interesting characteristics. With more reactive alkenes, such as 1-hexene, 2-methyl-1-pentene, 3,3-dimethyl-1-butene, and cyclopentene, the reaction exhibits first-order kinetics, first order in (9-BBN)2 and zero order in alkene. On the other hand, with less reactive alkenes, such as cyclohexene, 1-methylcyclohexene, and 2,3-dimethyl-2-butene, the reaction exhibits three-halves-order kinetics, first order in alkene and one-half order in (9-BBN)2. These kinetics can be accounted for in terms of the following mechanism:

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