FUNCTIONALLY SUBSITUTED SULFUR-CONTAINING COMPOUNDS. 9. REASTIONS OF 2-OXIRANES WITH ACETIC ANHYDRIDE AND ACETYL CHLORIDE

Article abstract of DOI:10.1007/BF00961238

Reaction of 2-<(organylthio)methyl>oxiranes with acetic anhydride gives a mixture of 3-(organylthio)-1,2-diacetoxypropane and 2-(organylthio)-1,3-diacetoxypropane, and with acetyl chloride a mixture of 2-chloro-3-(organylthio)-1-acetoxypropane and 3-chloro-2-(organylthio)-1-acetoxypropane.In both cases, the ratio of the isomers depends on the nature of the organylthio group and on the nature of the electrophile.