Limonene protonolysis

The protonolysis reaction tolerates functionalities such as halide or ether groups in the alkylborane. However, p-dialkylaminoalkylboron compounds undergo elimination to give alkenes under these conditions (see Section 3.10.1.2). ° " Also, systems which are intrinsically labile to either acid or heat, such as some terpenoids, may give problems. For example, enantiomerically pure limonene produces 1 -men-thene which is substantially racemized on hydroboration-protonolysis (Scheme 15). 

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