Tetrahedron

A fast procedure for the reduction of azides and nitro compounds based on the reducing ability of Sn (SR) 3-species

M Bartra, P Romea, F Urpí, J Vilarrasa

Index: Bartra, Marti; Romea, Pedro; Urpi, Felix; Vilarrasa, Jaume Tetrahedron, 1990 , vol. 46, # 2 p. 587 - 594

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Citation Number: 176

Abstract

Tin (II) complexes prepared by treatment of SnCl2or Sn (SR) 2 with appropriate amounts of RSH and Et3N appear to be the best reducing agents for azides (to amines) reported so far. These tin (II) complexes also reduce primary and secondary aliphatic nitro compounds to oximes, usually within minutes at rt or hours in cold, and tertiary aliphatic as well as aromatic nitro compounds to afford the corresponding hydroxylamines. In general, azides react ...