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35.1.1.1.1.5.2 Variation 2: Chlorination with Chlorine Monoxide

DOI: 10.1055/sos-SD-035-00004

Hartung, J.Science of Synthesis, (20073526.

Chlorine monoxide is a yellow-brown compound that melts at 120.6°C and boils at 2.0°C. It dissolves in carbon tetrachloride and is able to convert hydrocarbons into chloroalkanes if photolyzed with incandescent light (Scheme 9).[‌41‌] The yields for the majority of such transformations are unfortunately not given in the literature. Reference values, e.g. for chlorination of 1-chlorobutane, indicate that 1 equivalent of chlorine monoxide provides a total of 1.97 equivalents of chlorinated product, if photolyzed with a tenfold excess of a functionalized hydrocarbon. Its relative primary/secondary/tertiary CH reactivity index is slightly in favor of secondary chloroalkane formation, while tertiary derivatives are somewhat disfavored, if compared to chlorinations using tert-butyl hypochlorite (see Section 35.1.1.1, General Introduction, Table 2).

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