Reactions of 4-chloromethyl-1,3,2-dioxathiolane 2-oxides with sodium phenoxide. A reinvestigation

Article abstract of DOI:10.1007/BF02496348

The reactions of 4-chloromethyl-1,3,2-dioxathiolane 2-oxides with PhONa in EtOH are accompanied by ring opening under the action of the ethoxide ion rather than leading to a rearrangement of the starting molecule as has been assumed previously. Under conditions precluding competition with other nucleophiles, the phenoxide anion smoothly replaces the chlorine atom in chloromethyl-substituted cyclic sulfites.