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Hartung, J., Science of Synthesis, (2007) 35, 26.
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 C—H 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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References
[41] | Meeeee, M. M.; Meeeee, M., M. Me. Meee. Mee., (8888) 88, 888. |
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- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) 8/8, 888.
- 8.Meeeee-Meee, (8888) 8/8e, 888.