Unexpected conversion of alkyl azides to alkyl iodides and of aryl azides to N-tert-butyl anilines

J Maury, L Feray, MP Bertrand, A Kapat, P Renaud

Index: Maury, Julien; Feray, Laurence; Bertrand, Michele P.; Kapat, Ajoy; Renaud, Philippe Tetrahedron, 2012 , vol. 68, # 47 p. 9606 - 9611,6

Full Text: HTML

Citation Number: 6

Abstract

One of the most common methods for the synthesis of primary and secondary alkyl azides is the nucleophilic substitution of the corresponding alkyl halides (generally bromides) with sodium or lithium azide, in various solvents. 1 Only few publications are dealing with the reverse transformation, that is, the generation of an alkyl halide from an alkyl azide. Nitrosation of azidoalkanes with NO + BF 4 − leads to a mixture of fluoroalkanes, elimination products, and the ...