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N,N′-Bis(4-iodophenyl)diazene N-oxide

✍ Scribed by Krivokapić, Alexander ;Wilson, Craig J. ;Watkin, David J. ;Anderson, Harry L.

Publisher: International Union of Crystallography
Year: 2003
Tongue: English
Weight: 223 KB
Volume: 59
Category: Article
ISSN: 1600-5368
DOI: 10.1107/s1600536803013618

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✦ Synopsis

The title compound, C 12 H 8 I 2 N 2 O, was obtained as an unexpected product while attempting to protect N,N-dibutyl-4-iodoaniline as the N-oxide. It crystallizes as a layer structure.

Oxidation of (II) by hydrogen peroxide gives the N-oxide (III). This eliminates butene via a Cope reaction (Adams & Kovacic, 1974) before being oxidized again [to give (IV)] and undergoing a second elimination [to give (V)]. Di(hydroxyl)amine (V) then eliminates water to give nitrosamine (VI). From this point, it is likely that the mechanism is similar to that of the reaction between nitrosobenzene and phenylhydroxylamine (Becker & Sternson, 1980) [a radical mechanism is also seen in the presence of base (Russell et al.,

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N,N′-Bis(4-iodo­phenyl)­diazene N-oxide

✦ Synopsis

N,N′-Bis(4-iodophenyl)diazene N-oxide