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35.1.4.1.3 Method 3: Reaction with Chlorine Monoxide

DOI: 10.1055/sos-SD-035-00187

Pfeiffer, W. D.Science of Synthesis, (200735175.

Chlorine monoxide is an efficient ene-type chlorination reagent for alkenes under mild conditions.[‌16‌] For example, 4-chloro-1,5-dimethylhex-5-enyl acetate (17) is obtained by dropwise addition of a solution of chlorine monoxide in carbon tetrachloridediethyl ether to 1,5-dimethylhex-5-enyl acetate (16) at room temperature (Scheme 5). The treatment of the azetidin-2-one derivative 18 with chlorine monoxide in a mixture of carbon tetrachloridedichloromethanewater affords the corresponding chloride 19 in 85% yield.[‌16‌]

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