Science of Synthesis

Boysen, M. M. K., Science of Synthesis, (2010) 41, 449.

General Introduction

This section describes the synthesis of aliphatic diazene oxides (alkyl and alk-1-enyl derivatives), which is the IUPAC-approved nomenclature for compounds that are still colloquially called azoxy compounds. Especially in the papers concerned with their synthesis, which in many cases date back to the 1960s and 1970s, several nomenclature systems are encountered and to clarify matters, the most important alternative names and stereochemical descriptors of both symmetrical (identical substituents at both nitrogen atoms) and unsymmetrical aliphatic diazene oxides are shown in ‌Table 1‌. The relationship between the structures shown in entries 1 and 2 is that of stereoisomers, whereas the relationship between the molecules in entries 3 and 4 is that of regioisomers. The cis and trans descriptors used in older names describe the relationship between the alkyl groups attached to the nitrogen atoms of the diazene oxide. The alkyl group attached to the oxygen-bearing nitrogen atom of the diazene oxide is referred to as the proximal group, and that attached to the other nitrogen atom as the distal group. Aliphatic diazene oxides have been covered in Houben–Weyl, Vol. 10/2, pp 787–801 and Vol. E 16d, pp 133–141. Azoxyarenes and mixed aromatic–aliphatic azoxy compounds are described in Science of Synthesis, Vol. 31b [Arene—X (X = N, P) (Section ‌31.24‌31.24)].

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References