The Journal of Organic Chemistry

Photochemistry of (o-methylphenyl) alkadienes: attempted intramolecular trapping of the resulting o-xylylenes

JM Hornback, RD Barrows

Index: Hornback, Joseph M.; Barrows, Russell D. Journal of Organic Chemistry, 1983 , vol. 48, # 1 p. 90 - 98

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Citation Number: 4

Abstract

The photochemistry of a series of o-methylphenyl dienes was investigated in order to determine if the resulting o-xylylenes could be trapped in an intramolecular Diels-Alder reaction in synthetically useful yields. Irradiation of 3 gave meta-isomer 4 as the major product along with lower yields of double bond migration product 5 and the desired cycloadduct 6. The best yield of 6 (24%) was obtained by irradiation of 3 with a low- ...