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31.32.1.1.3 Variation 3: By Reaction with Dichlorine Monoxide

DOI: 10.1055/sos-SD-031-01909

Chiara, J. L.Science of Synthesis, (2007311731.

Dichlorine monoxide (Cl2O) is a highly reactive chlorinating reagent that produces only water as a byproduct. Like chlorine (see Section 31.32.1.1.1), dichlorine monoxide is able to quantitatively N-chlorinate highly deactivated arylamines 18 in a short period of time (<15min).[‌13‌] Thus, 2-nitroanilines 18 (R1=NO2), which do not react with calcium hypochlorite and react extremely slowly with tert-butyl hypochlorite, are quantitatively N-monochlorinated using a substoichiometric amount (0.5 equiv) of the reagent (Scheme 8). The N-chlorination reaction is usually performed in carbon tetrachloride at room temperature. A desiccant (Na2SO4) is added in order to remove the water formed and avoid hydrolytic decomposition of the N-chloroanilines 19. This reaction has been reported to be exceedingly slow when the dichlorine monoxide is completely free of molecular chlorine.[‌32‌]

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