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31.22 Product Class 22: Nitrosoarenes

DOI: 10.1055/sos-SD-031-01513

Rück-Braun, K.; Priewisch, B.Science of Synthesis, (2007311321.

General Introduction

The synthesis of aromatic C-nitroso compounds (Ar1NO, Ar1=aryl, hetaryl) has been reviewed in HoubenWeyl, Vol.10/1, p1017 and Vol.E 16/2a, p979, and has been the subject of various other reviews, including one that covers the literature up to 2004.[‌1‌] The synthesis and the properties of di- and polynitroso compounds have also been surveyed.[‌2‌] Nitrosoarenes are highly reactive compounds, many of them being light sensitive, a fact that complicates the synthesis and isolation of compounds of this class. Many nitrosoarenes are volatile under reduced pressure, even at room temperature, and this should be borne in mind when concentrating or drying nitroso compounds. On the other hand, steam-distillation and sublimation are mild methods for the purification of many nitrosoarenes. Most nitrosoarenes form colorless dimers in the solid state, while in solution an equilibrium between the monomeric and the E- and Z-dimeric forms exists (Scheme 1). Generally, the blue- or green-colored monomeric form dominates, and the population of the equilibrium depends on the substituents, and can be determined by means of IR and NMR spectroscopy.[‌3‌,‌4‌]

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