Hydroboration of terpenes I. The selective hydroboration of myrcene with Disiamylborane (cas 1069-54-1)

Add time:07/25/2019    Source:sciencedirect.com

The reaction of disiamylborane with myrcene (7-methyl-3-methylene-1,6-octadiene) occurs selectively to place the boron atom at the 1-position. Oxidation of the resulting organoborane with alkaline hydrogen peroxide yields myrcenol (7-methyl-3-methylene-6-octen-1-ol) identified by infrared and nuclear magnetic resonance spectra. Further hydroboration of myrcenol with disiamylborane, or dihydroboration of myrcene with the reagent, results in selective reaction at the 3-methylene group. Oxidation of the products yields the diol, 7-methyl-3-hydroxymethyl-6-octan-1-ol. Consequently, the three double bonds of myrcene exhibit a tendency to undergo attack in the order, RCH2CH2 > RR′CCH2 > R2CCHR′, as predicted from competitive experiments with simple model systems.

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