Sulfenyl Chlorides
Sulfenyl Chlorides
Sulfenyl chlorides, R-S-Cl, are group of organosulfur compounds having the functional group ûS-Cl, wherein R is an alkyl or an aryl group. Sulfenyl chlorides behave as a pseudohalogen and are a source of alkylthio and arylthio groups (RS-). These groups can be easily introduced by reacting sulfenyl chloride with a carbanion or its enolate, adding across double bonds in alkenes, allenes and alkynes.
Sulfenyl chlorides find use in the preparation of sulfenamides. Some sulfenyl chlorides such as tritylsulfenyl chloride and o-nitrophenylsulfenyl chloride are used as nitrogen protecting groups, for example, for aminoacid esters. Such N-sulfenyl protections are important during the lengthening of peptides and are easily deprotected later.
Sulfenyl chlorides are industrially important in the modification of wool and preparation of heterocyclic compounds. In the rubber industry, sulfenyl chlorides are employed as curing agents while some sulfenyl chlorides like dichlorofluoromethanesulfenyl chloride and chlorodifluoromethanesulfenyl chloride are useful reagents in the synthesis of bioactive compounds that protect plants. Perfluoroalkane sulfenyl chlorides are an important group of chemicals used in pharmaceutical and agrochemical industries that are used to introduce perfluoroalkyl groups on to the active molecule.
