Journal of the Chemical Society. Perkin transactions I p. 501 - 505 (1996)
Update date:2022-09-26
Topics:
Glossop, Paul
Jones, David W.
Contrary to earlier observations the diene 1 reacts readily in Diels-Alder additions. With N-methylmaleimide the stereoisomeric adducts 10a and 10b are formed in equal quantities. With maleic anhydride, ring-opening accompanies adduction to give 11 and two stereoisomers of gross structure 12. Dienes 1,9 (X = OMe) and 9 (X = H) react at similar rates with N-methylmaleimide, discounting the alleged intramolecular retardation due to through space interaction between the hydroxy group and the diene system.
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