10.1021/acs.orglett.7b00077.s002 Daniele Canestrari Daniele Canestrari Stefano Lancianesi Stefano Lancianesi Eider Badiola Eider Badiola Chiara Strinna Chiara Strinna Hasim Ibrahim Hasim Ibrahim Mauro F. A. Adamo Mauro F. A. Adamo Desulfurative Chlorination of Alkyl Phenyl Sulfides American Chemical Society 2017 nitro compounds Desulfurative Chlorination enantioenriched benzylic sulfides Alkyl Phenyl Sulfides PhICl 2 enantioenriched chloro-Michael adducts nucleophilic chlorination chlorides proceeds elimination-sensitive β- chloro carbonyl alkyl phenyl sulfides dichloro -λ 4 2017-02-02 20:18:18 Dataset https://acs.figshare.com/articles/dataset/Desulfurative_Chlorination_of_Alkyl_Phenyl_Sulfides/4614733 The chlorination of readily available secondary and tertiary alkyl phenyl sulfides using (dichloroiodo)­benzene (PhICl<sub>2</sub>) 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-λ<sup>4</sup>-sulfurane intermediate is proposed.