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.