Science of Synthesis

Collier, S. J.; Xiang, W., Science of Synthesis, (2010) 41, 651.

General Introduction

This contribution covers the preparation of N,N-dihaloamines ‌1‌ (‌Scheme 1‌), and is divided into sections based upon the halogens present in the products. The types of functionality discussed include difluoroamines, dichloroamines, dibromoamines, diiodoamines, and mixed dihaloamines. A number of dihaloamines bearing two nonidentical halogen substituents have been reported, and some are known from only a handful of examples. Of the various theoretically possible mixed dihaloamines, at the time of writing, fluoroiodoamines, chloroiodoamines, and bromoiodoamines are not known, although there is a report discussing N-chloro-N-iodolactams (1,2-benziodazol-3-ones).[‌1‌] Only aliphatic dihaloamines are considered, as N-haloarylamines are covered in Science of Synthesis, Vol. 31b [Arene—X (X = N, P) (Section ‌31.32‌)], N-haloenamines are covered in Vol. 33 [Ene—X Compounds (X = S, Se, Te, N, P) (Section ‌33.4.10‌)], and N-haloamides are discussed in Vol. 21 [Three Carbon–Heteroatom Bonds: Amides and Derivatives; Peptides; Lactams (Section ‌21.13.8‌21.13.8)]. Previously published information on N,N-dihaloamines can be found in Houben–Weyl, Vol. E 16a/2, pp 893–949. Note that this review does not give comprehensive coverage, but attempts to cover all the important methods of preparing the title compounds.

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References