Organic Letters

Metalation of Iminium Ions Formed in the Reaction of Tertiary Amines with TiCl4

P Bharathi, M Periasamy

Index: Bharathi, Pandi; Periasamy, Mariappan Organic Letters, 1999 , vol. 1, # 6 p. 857 - 859

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Citation Number: 32

Abstract

In 1955, it was reported that the reaction of TiCl 4 with N(CH 3 ) 3 leads to “(CH 3 ) 2 NCH 2 Cl” and TiCl 3 . 5 Accordingly, this transformation may be explained by the tentative mechanistic pathway involving iminium ion intermediate as outlined in Scheme 1. The reaction of TiCl 4 with trialkylamine may proceed with the initial formation of an amine−TiCl 4 complex. Elimination of β-hydrogen from the amine moiety of this complex would produce the iminium ion ...