Tetrahedron p. 12907 - 12922 (1998)
Update date:2022-08-23
Topics:
Fielder, Simon
Rowan, Daryl D.
Sherburn, Michael S.
Isomeric unsaturated alcohols (8), (16), (18) and (20), on exposure to hydrogen peroxide or water in the presence of an acid catalyst, undergo exceptionally regio- and stereoselective substitution reactions to form hydroperoxide (3) and alcohol (8) respectively. E/Z isomeric ratios of transposition products indicate that the intermediate acyclic carbocations (21) and (22) are not interconverting under the reaction conditions. Practical syntheses of α-farnesene autoxidation products have been developed based on these transposition reactions.
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