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

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 r ather than leading to a rearrangement of the starting molecule as has been assumed previously. Under conditions precluding competition with other nucl eophiles, the phenoxide anion smoothly replaces the chlorine atom in chloro methyl-substituted cyclic sulfites.