75600-37-2Relevant articles and documents
A novel phenylsulfenylation of unsaturated acids or alcohols by methyl phenyl sulfoxide and substoichiometric (COCl)2
Liang, Sen,Liu, Yongguo,Sun, Baoguo,Tian, Hongyu,Wang, Hao,Wang, Yinong,Wang, Yutong,Xiang, Fan
supporting information, (2022/01/03)
Phenylsulfenylation of unsaturated acids and alcohols has been achieved by methyl phenyl sulfoxide (PhSOCH3) and substoichiometric (COCl)2 in CH3CN. The corresponding cyclization products, lactones with a phenylthio group from unsaturated acids were obtained in mediate to good yields, whereas the cyclic ethers with a phenylthio group from unsaturated alcohols in relatively low yields. PhSOH was proposed to be the key active species for phenylsulfenylation, which was generated in situ by the reaction of PhSOCH3 with substiochiometric amount of (COCl)2. Anhydrous HCl could replace (COCl)2 in the reactions to give the comparable results.
CYCLIC ETHER SYNTHESIS: SULFENYLETHERIFICATION WITH BENZENESULFENYL CHLORIDE/N,N-DIISOPROPYLETHYLAMINE AND SULFENATE ESTER CYCLOADDITIONS
Tuladhar, Sudersan M.,Fallis, Alex G.
, p. 1833 - 1837 (2007/10/02)
A general method for the formation of the cyclic ethers 9, 10, 13, 14, 16 and the lactone 30 is described.The procedure employs benzenesulfenyl chloride prepared in situ in acetonitrile and N,N-diisopropylethylamine to generate a thiiranium (episulfonium) ion intermediate from which the cyclic products arise by internal nucleophilic displacement.In the special case of the norbornene alcohols 1 and 2 the oxethanes 5 and 6 are formed by intramolecular sulfenate ester cycloaddition.
