Reactions of 4-chloromethyl-1,3,2-dioxathiolane 2-oxides with sodium phenoxide. A reinvestigation |
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| Authors: | Z A Bredikhina A V Pashagin A A Bredikhin |
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| Institution: | (1) A. E. Arbuzov Institute of Organic and Physical Chemistry, Kazan Research Center of the Russian Academy of Sciences, 8 ul. Akad. Arbuzova, 420088 Kazan, Tatarstan, Russian Federation |
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| Abstract: | 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.
Published inIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 10, pp. 1774–1777, October, 2000. |
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| Keywords: | cyclic sulfites nucleophilic substitution sodium phenoxide ethoxide anion |
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