Intramolecular acyl radical-alkene addition reactions: macrocyclization reactions

DL Boger, RJ Mathvink

Index: Boger, Dale L.; Mathvink, Robert J. Journal of the American Chemical Society, 1990 , vol. 112, # 10 p. 4008 - 4011

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Citation Number: 67

Abstract

Abstract: The generation of acyl radicals from phenyl selenoesters and the scope of their participation in macrocyclization free-radical alkene addition reactions are detailed. The studies illustrate that large ring w-acryloyl radical cyclizations proceed at rates competitive with those of 5-exo-trig cyclization of 5-hexenoyl radicals and that exceed those of 6-exo-or 7-endo-trig cyclization of 6-heptenoyl radicals, thus providing an effective ...