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Paper | Regular issue | Vol 36, No. 5, 1993, pp.1059-1064
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6274
Reaction of 1-Methylpyrrole with 1,3-Dichloro-5,5-disubstituted Hydantoins: Products and AM1 Study of Intermediates

Michael De Rosa,* Edward Melenski, and Andrew J. Holder

*Department of Chemistry, The Pennsylvania State University Delaware County Campus, 25 Yearsley Mill Road, Media, PA 19063, U.S.A.

Abstract

The reaction of 1-methylpyrrole with 1,3-dichloro-5,5-dimethylhydantoin gave 3-(1-methyl-1H-pyrrol-2-yl)-5,5-dimethylhydantoin and 1,3-di-(1-methyl-1H-pyrrol-2-yl)-5,5-dimethylhydantoin as products. In contrast reaction with 1,3-dichloro-5-methyl-5-phenylhydantoin (3) or 1,3-dichloro-5,5-diphenylhydantoin (4) gave only the monopyrroylhydantoin derivatives. This difference was attributed to a steric interaction between the substituents on C-5 and N1.