Phenol undergoes thermal 2,5-cycloaddition of N-phenylmaleimide to give endo- and exo-bicyclo-octenones (3) and (4) respectively, and a homopolymer of the maleimide; use of N-(p-methoxyphenyl)maleimide minimizes polymer formation, and gives a combined cycloadduct yield of 60% in the case of p-cresol.
D. Bryce-Smith, A. Gilbert, I. S. McColl and P. Yianni, J. Chem. Soc., Chem. Commun., 1984, 951 DOI: 10.1039/C39840000951
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