caa a22 4500 475761685 CHVBK 20180406123553.0 cr unu---uuuuu 170329e20000501xx s 000 0 eng 10.1007/BF02494713 doi (NATIONALLICENCE)springer-10.1007/BF02494713 Functionally substituted sulfur-containing compounds [Elektronische Daten] 12. Reactions of 2-[(organylthio)methyl]oxiranes with aliphatic alcohols in the presence of boron trifluoride etherate [V. Kalugin, V. Litvinov] Reactions of 2-[(organylthio)methyl]oxiranes with aliphatic alcohols in the presence of catalytic amounts of BF3·Et2O are accompanied by 1,2-migration of the organylthio group to give mixtures of 2-alkoxy-3-(organylthio)propan-1-ols and 3-alkoxy-2-(organylthio)propan-1-ols. The ratio of these isomers is significantly influenced by the structure of the alcohol and the nature of the organylthio group. The proposed reaction mechanism includes the formation of a thiiranium intermediate and its subsequent transformations. Kluwer Academic/Plenum Publishers, 2000 2-[(organylthio)methyl]oxiranes nationallicence aliphatic alcohols nationallicence boron trifluoride etherate nationallicence isomers nationallicence steric factor nationallicence thiiranium intermediate nationallicence Kalugin V. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Litvinov V. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/5(2000-05-01), 879-885 1066-5285 49:5<879 2000 49 11172 https://doi.org/10.1007/BF02494713 text/html Onlinezugriff via DOI 1 research-article jats NATIONALLICENCE 856 40 https://doi.org/10.1007/BF02494713 text/html Onlinezugriff via DOI NATIONALLICENCE 700 1- Kalugin V. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 700 1- Litvinov V. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 117913, Moscow, Russian Federation aut NATIONALLICENCE 773 0- Russian Chemical Bulletin Kluwer Academic Publishers-Plenum Publishers 49/5(2000-05-01), 879-885 1066-5285 49:5<879 2000 49 11172 Metadata rights reserved Springer special CC-BY-NC licence nationallicence BK010053 XK010053 XK010000 NATIONALLICENCE NATIONALLICENCE NL-springer