Abstract
Abstract On oxidation with tert-butyl chromate, d-p-menthene-3 gave d-carvenone as a main product and dl-p-menthen-3-one-5 as a by-product. In this oxidation, it is found that, when an endocyclic double bond is in the position between C(3) and C(4) in monocyclic terpenes of p-menthane type, two active methylenes adjacent to the endocyclic double bond are selectively oxidized to carbonyls as in the case of the terpenes containing an endocyclic double bond in the position between C(1) and C(2), and that, between the two active methylenes, the one remote from the isopropyl group attached to C(4) is preferentially attacked rather than the other which is close to the same group.
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