Tetrahedron

Use of hexamethylphosphoramide chmpa in the alkylation of aromatic amines: synthesis of azetidines, pyrrolidines, piperidines and hexahydroazepines

E Juaristi, D Madrigal

Index: Juaristi, Eusebio; Madrigal, Domingo Tetrahedron, 1989 , vol. 45, # 3 p. 629 - 636

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Citation Number: 28

Abstract

The direct alkylation of p-toluidine, as a model of aromatic amines, with 1, 3-, 1, 4-, 1, 5-and 1, 6-ditosylates,-dibromides or-dimesylates in HMPA as solvent affords the corresponding cyclic amines. The convenience of this reaction and some observed limitations are discussed.