Tetrahedron

Photo-induced reactions—XVIII: The photochemical transformation of 4-hydroxy-and 4-acetoxy-2, 5-cyclohexadienones

T Matsuura, K Ogura

Index: Matsuura,T.; Ogura,K. Tetrahedron, 1968 , vol. 24, p. 6167 - 6175

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Citation Number: 5

Abstract

The UV irradiation of 2, 4, 6-tri-t-butyl-4-hydroxy-2, 5-cyclohexadienone (I) in petroleum ether yielded the diketone V (11%) and the enedione VII (54%) in addition to the cyclopentenone VIII (3%) and the bicyclopentanone X (8%). The formation of V and VII can be rationalized by considering a common intermediate, the lumi-type ketone III. This result indicates that 4-hydroxy-2, 5-cyclohexadienones undergo photorearrangement similar to ...