Bulletin of the Chemical Society of Japan

Low temperature photolysis of o-benzoquinones. Spectroscopic detection of cyclopentadienones and bis-ketenes.

H Tomioka, H Fukao, Y Izawa

Index: Tomioka,H. et al. Bulletin of the Chemical Society of Japan, 1978 , vol. 51, p. 540 - 543

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Citation Number: 6

Abstract

The photodecarbonylation of o-benzoquinone to cyclopentadienone at low temperature was monitored by infrared and ultraviolet spectra which showed that the reaction is highly sensitive to substituents. 3, 5-Di-t-butyl-o-benzoquinone undergoes clean decarbonylation to give cyclopentadienone under irradiation at− 170° C. Similar irradiation of 4-t-butyl-, 4- methyl-, 3-methyl-, and unsubstituted o-benzoquinones also leads to decarbonylation to ...