Tetrahedron

Regiochemistry of the cycloadditions of diphenylnitrilimine to coumarin, 3-ethoxycarbonyl and 3-acetyl coumarins: A reinvestigation

T Fathi, ND An, G Schmitt, E Cerutti, B Laude

Index: Fathi, Toufik; Dinh An, Nguyen; Schmitt, Gerard; Cerutti, Ernest; Laude, Bernard Tetrahedron, 1988 , vol. 44, # 14 p. 4527 - 4536

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Citation Number: 19

Abstract

The cycloaddition reactions of diphenylnitrilimine to coumarin, 3-ethoxycarbonyl and 3- acetylcoumarins were studied. The observed regiochemistry of the reaction with the coumarin 4a was the same as the one suggested by other researchers. For the coumarins 4b and 4c bearing an electron withdrawing group at the 3-carbon atom, our results invalidate the previously reported regiochemistry. The presence of an electron- ...