105854-98-6Relevant articles and documents
Desulfurative Chlorination of Alkyl Phenyl Sulfides
Canestrari, Daniele,Lancianesi, Stefano,Badiola, Eider,Strinna, Chiara,Ibrahim, Hasim,Adamo, Mauro F. A.
supporting information, p. 918 - 921 (2017/02/26)
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.