Science of Synthesis

Rück-Braun, K.; Priewisch, B., Science of Synthesis, (2007) 31, 1401.

General Introduction

This section covers the synthesis of diaryldiazene oxides ‌1‌ (R1 = aryl) and monoaryldiazene oxides ‌1‌ (R1 = alkyl) (‌Scheme 1‌). The preferred IUPAC name diazene oxide replaces the older name azoxyarene, and will be used in this section. However, for a search of published literature, the reader should also refer to names derived from the parent azoxybenzene compound. The synthesis of diaryldiazene oxides has been reviewed previously in Houben–Weyl, Vol. 10/3, pp 749–776 and Vol. E 16d, pp 119–133, and that of monoaryldiazene oxides in Vol. 10/3, pp 471–489 and Vol. E 16d, pp 133–141. Mono- and diaryldiazene oxides are of interest because of their liquid crystal properties and as intermediates for the synthesis of dyes (see Section ‌31.25‌, on azoarenes). The diazene oxide moiety is also found in some natural products.[‌1‌,‌2‌] Diazene oxides may exist in two stereoisomeric forms (Z)-‌1‌ and (E)-‌1‌, which can interconvert chemically and photochemically (‌Scheme 1‌). In the dark, (E)-diazene oxides (E)-‌1‌ are converted into the thermally more stable Z-isomers (Z)-‌1‌ (‌Scheme 1‌). The photochemistry of diaryldiazene oxides has been reviewed briefly.[‌3‌]

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References

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• 8.Meeeee-Meee, (8888) 88/8, 888.
• 8.Meeeee-Meee, (8888) M 88e8, 888.