- Desulfurative Chlorination of Alkyl Phenyl Sulfides
-
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.
- Canestrari, Daniele,Lancianesi, Stefano,Badiola, Eider,Strinna, Chiara,Ibrahim, Hasim,Adamo, Mauro F. A.
-
supporting information
p. 918 - 921
(2017/02/26)
-
- Replacement of the Activated Nitro Group by a Phenylthio Group
-
The nitro group, activated by a carbonyl group, alkoxycarbonyl group or a phenyl group, can be replaced by a phenylthio group in the reaction with benzenethiol or its potassium salt.This reaction proceeds in the electron transfer mechanism, and is applicable to the general syntheses of α-phenylthio ketones, α-phenylthio carboxylic esters and α-phenylthio alkylbenzenes from primary nitro compounds.
- Miyake, Hideyoshi,Yamamura, Kimiaki
-
-