The Journal of Organic Chemistry

Acid-mediated rearrangement of acylpyrroles

JR Carson, NM Davis

Index: Carson, John R.; Davis, Nancy M. Journal of Organic Chemistry, 1981 , vol. 46, # 5 p. 839 - 843

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Citation Number: 51

Abstract

Treatment of ketone If with acid brought about migration of the acyl group specifically to the 3- position of the pyrrole ring. This structure is consistent with the observed 1.5% coupling between the pyrrole ring protons. In contrast to the N-alkyl compounds 1 which were converted by acid completely to isomer 2, heating either a 2-acylpyrrole (3) or a 3- acylpyrrole (4) bearing hydrogen on nitrogen in strong anhydrous acid gave rise to an ...

~78%

~13%

~44%

~41%

~43%

~80%

~64%

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