Synthesis and reactions of. alpha.-carbomethoxy-N-phenylmaleimide and related electrophilic ethylenes

…, M Abdelkader, AB Padias, HK Hall Jr

Index: Evans, Stacy B.; Abdelkader, Mohamed; Padias, Anne Buyle; Hall, H. K. Journal of Organic Chemistry, 1989 , vol. 54, # 12 p. 2848 - 2852

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Citation Number: 8

Abstract

The synthesis of a-carbomethoxy-N-phenylmaleimide(CNPM) was accomplished by way of a Diels-Alder precursor from a-carbomethoxymaleic anhydride and cyclopentadiene, conversion of the anhydride functionality to N-phenylmaleimide, and finally thermolysis. Reactions of this highly electrophilic new olefin with donor olefins were studied. The Diels- Alder product with cyclopentadiene and unstable [2+ 21 cycloadducts with N- ...