The Chemistry of Laurenene. VI. An Investigation of the Widely Differing Reactivity of a Pair of Epimeric Keto Esters

Abstract

X-ray crystallography and two-dimensional n.m.r. techniques have been used to establish the conformations of the epimeric keto esters (1) and (3), derived from cleavage of ring A of lauren-1-ene (2). This information has been used to rationalize the disparate reactivity of the keto functions of (1) and (3) in acid-catalysed carbocation rearrangements and with lithium aluminium hydride. The structures of two new rearranged ethers derived from (1) are also discussed.