The Journal of Organic Chemistry

Substituent effects on the photorearrangements of 4-alkoxy-4-carbomethoxy-3-methoxy-2, 5-cyclohexadien-1-ones

AG Schultz, RE Harrington

Index: Schultz, Arthur G.; Harrington, Roger E. Journal of Organic Chemistry, 1991 , vol. 56, # 22 p. 6391 - 6394

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Citation Number: 8

Abstract

Enantiomerically enriched 4-carbomethoxy-3, 4-dimethoxy-2, 5-~ yclohexadien-l-one (1) undergoes a completely diastereoselective (but not enantiospecific) type A photorearrangement at 366 nm to give 6-carbomethoxy-4, 6-dimethoxybicyclo [3.1. 0'~ 6] hex-3-en-2-one (2) in 81% isolated yield. A chiral NMR shift study indicates that. 1 undergoes partial loss of absolute configuration at C (4) during irradiation. ...