Science of Synthesis

Boysen, M. M. K., Science of Synthesis, (2010) 41, 437.

General Introduction

All stable N-nitrosoamines are formally derived from secondary amines. Indeed, nitrosation of secondary amines is one of the most important synthetic routes toward these compounds; on the other hand, dealkylating nitrosation of tertiary amines may also lead to N-nitrosoamines. In contrast, N-nitrosation of primary amines exclusively leads to formation of diazonium compounds (alkane- and alkenediazonium compounds are discussed in Section ‌41.7‌, for arenediazonium compounds, see Science of Synthesis, Vol. 31b [Arene—X (X = N, P) (Section ‌31.23‌)]). N-Nitrosoamines can carry alkyl as well as aryl residues (‌Scheme 1‌). The first synthesis of an N-nitrosoamine was reported in the middle of the 19th century.[‌1‌] These compounds have been covered previously in Houben–Weyl, Vol. E 16a, pp 1137–1146.

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References