ol7b00077_si_003.cif (860.27 kB)
Desulfurative Chlorination of Alkyl Phenyl Sulfides
dataset
posted on 2017-02-02, 20:18 authored by Daniele Canestrari, Stefano Lancianesi, Eider Badiola, Chiara Strinna, Hasim Ibrahim, Mauro F. A. AdamoThe 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.