The reaction of N-magnesium derivatives of pyrroles with N-mesylchloromethylpyrroles: A synthesis of dipyrrylmethanes

AD Abell, BK Nabbs, AR Battersby

Index: Abell, Andrew D.; Nabbs, Brent K.; Battersby, Alan R. Journal of Organic Chemistry, 1998 , vol. 63, # 23 p. 8163 - 8169

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Citation Number: 26

Abstract

Attachment of an alkyl-or arylsulfonyl group at the nitrogen atom of a pyrrole reduces the aromaticity and electron availability of the system. This is confirmed by the structure of an N- tosylated chloromethylpyrrole determined by X-ray crystallography. In agreement, N- mesylated chloromethylpyrroles are handleable materials which react smoothly with N- magnesium derivatives of pyrroles to provide a novel route for synthesis of ...