Pyrrole chemistry. XXVIII. Substitution reactions of 1-(phenylsulfonyl) pyrrole and some derivatives

HJ Anderson, CE Loader, RX Xu, N Lê…

Index: Anderson, Hugh J.; Loader, Charles E.; Xu, Ru Xun; Le, Nghia; Gogan, Niall J.; et al. Canadian Journal of Chemistry, 1985 , vol. 63, p. 896 - 902

Full Text: HTML

Citation Number: 98

Abstract

The preparative value of the 1-(phenylsulfonyl) N-blocking and directing group for the synthesis of 3-acylpyrroles has been further evaluated. Acetylation and benzoylation are strongly regiospecific and give good yields. However, the regiospecificity is not general and other substitution reactions give mixtures of 2-and 3-substitution or even mostly 2- substitution. Friedel and Crafts tert-butylation gives 3-tert-butyl-1-(phenylsulfonyl) pyrrole ...