Oxidative radical cyclization to pyrroles under reducing conditions. Reductive desulfonylation of α-sulfonylpyrroles with tri-n-butyltin hydride

Y Antonio, ME De La Cruz, E Galeazzi…

Index: Antonio, Yulia; Cruz, Ma. Elizabeth De La; Galeazzi, Edvige; Guzman, Angel; Bray, Brian L.; et al. Canadian Journal of Chemistry, 1994 , vol. 72, # 1 p. 15 - 22

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Citation Number: 68

Abstract

1-(2-Bromobenzyl)-2-alkanesulfonylpyrroles (1 c, 1 d) and 1-(4-bromobutyl)-2- methylsulfonfylpyrrols (8) undergo oxidative radical cyclization with partial or complete reductive desulfonylation to the pyrrolizidine derivatives 5 and 9 by an AIBN initiated reaction with tri-n-butyltin hydride. These cyclizations are suggested to proceed via a pseudo SRN1 process involving radical addition to the α position of the pyrrole nucleus ...

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