Tetrahedron

CuCl-catalyzed radical cyclisation of N-α-perchloroacyl-ketene-N, S-acetals: a new way to prepare disubstituted maleic anhydrides

A Cornia, F Felluga, V Frenna, F Ghelfi, AF Parsons…

Index: Cornia, Andrea; Felluga, Fulvia; Frenna, Vincenzo; Ghelfi, Franco; Parsons, Andrew F.; Pattarozzi, Mariella; Roncaglia, Fabrizio; Spinelli, Domenico Tetrahedron, 2012 , vol. 68, # 29 p. 5863 - 5881

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Abstract

The copper-catalyzed radical cyclization (RC) of N-α-perchloroacyl cyclic ketene-N, X (X= O, NR, S)-acetals was studied. While the RC of N-acyl ketene-N, O-acetals was unsuccessful, the 5-endo cyclization of the other ketene acetals provided much better results, with the following order of cyclization efficiency: hexa-atomic cyclic ketene-N, NR-acetals