The chemistry of terpenes. Part III. The conversion of 2βH-pinan-3-one into 2βH-pinan-4-one
Abstract
The ketone transposition sequence for the conversion of 2βH-pinan-3-one (pinocamphone) into 2βH-pinan-4-one (trans-verbanone)via the reduction of 4-benzylidene-2βH-pinan-3-one with lithium aluminium hydride–lauminium chloride was unsuccessful owing to the failure of the reduction procedure to give 4-benzylidene-2βH-pinane. However, an alternative procedure via 3-acetoxy-4-benzylidene-2βH-pinane readily gave 2βH-pinan-4-one.