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41.5.1.1.1 Method 1: Oxidation of Diazenes

DOI: 10.1055/sos-SD-041-00457

Boysen, M. M. K.Science of Synthesis, (201041450.

A general method for the preparation of symmetrical aliphatic diazene oxides 3 is the oxidation of the corresponding 1,2-diazenes 2, more commonly known as azo compounds. Organic peroxy acids, such as peroxybenzoic,[‌15‌,‌16‌] peracetic,[‌17‌,‌18‌] and 3-chloroperoxybenzoic acid[‌2‌,‌18‌] are the reagents of choice for this transformation (Scheme 2). Strongly acidic reaction conditions (e.g., hydrogen peroxide in acetic acid and nitric acid) lead to rapid isomerization of the aliphatic diazene compounds into hydrazones. The geometry of the diazene starting material is retained during the oxidation reaction, allowing selective preparation of both Z- and E-diazene oxides.

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