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Desulfurative Chlorination of Alkyl Phenyl Sulfides

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journal contribution
posted on 2017-02-02, 20:18 authored by Daniele Canestrari, Stefano Lancianesi, Eider Badiola, Chiara Strinna, Hasim Ibrahim, Mauro F. A. Adamo
The chlorination of readily available secondary and tertiary alkyl phenyl sulfides using (dichloroiodo)­benzene (PhICl2) is reported. This mild and rapid nucleophilic chlorination is extended to sulfa-Michael derived sulfides, affording elimination-sensitive β-chloro carbonyl and nitro compounds in good yields. The chlorination of enantioenriched benzylic sulfides to the corresponding inverted chlorides proceeds with high stereospecificity, thus providing a formal entry into enantioenriched chloro-Michael adducts. A mechanism implying the formation of a dichloro-λ4-sulfurane intermediate is proposed.

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