Functionally substituted sulfur-containing compounds 12. Reactions of 2-[(organylthio)methyl] oxiranes with aliphatic alcohols in the presence of boron trifluoride etherate

Reactions of 2-[(organylthio)methyl]oxiranes with aliphatic alcohols in the presence of catalytic amounts of BF3. Et2O are accompanied by 1,2-migratio n of the oganylthio group to give mixtures of 2-alkoxy-3-(organylthio)propa n-1-ols and 3-alkoxy-2-(organylthio)propan-1-ols. The ratio of these isomer s is significantly influenced by the structure of the alcohol and the natur e of the organylthio group. The proposed reaction mechanism includes the fo rmation of a thiiranium intermediate and its subsequent transformations.