Tetrahedron

Kinetically distinct triplets in the photorearrangement of 2-phenylcyclohexanone to cis-and trans-6-phenyl-5-hexenals

PJ Wagner, TJ Stratton

Index: Wagner, Peter J.; Stratton, Thomas J. Tetrahedron, 1981 , vol. 37, # 19 p. 3317 - 3322

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Citation Number: 17

Abstract

A reinvestigation of the photochemistry of 2-phenylcyclohexanone reveals that the two aldehyde products, cis-and trans-6-phenyl-5-hexanal, come from triplets of different lifetimes. That the two distinct triplets are not simply the two conformers with phenyl axial and equatorial is demonstrated by the similar behavior of cis-4-t-butyl-2-phenylcyclohexanone. The trans isomer of this ketone is photostable. It is concluded that trans-enal arises by an ...