The Journal of Organic Chemistry

Pivaloylation of N-methylpyrrole. Formation of a novel 3, 4-diacylation product

MC Harsanyi, RK Norris

Index: Harsanyi, Michael C.; Norris, Robert K. Journal of Organic Chemistry, 1987 , vol. 52, # 11 p. 2209 - 2213

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Citation Number: 12

Abstract

The pivaloylation of N-methylpyrrole (1) with pivaloyl chloride and tin (1V) chloride in benzene or 1, 2-dichloroethane at 20 “C gives mixtures of mono-and dipivaloylated pyrroles. N-Methyl-2-pivaloylpyrrole (2) is formed in only trace amounta and the 3-isomer 3 is the predominant monosubstituted product. Substantial amounts of N-methyl-2, 4- dipivaloylpyrrole (4) and smaller amounts of the 3, 4-isomer 5 are also formed. Facile ...