Ethyl dimethyl sulfonium iodide

P3.03.32. SODIUM ETHOXIDE AND ETHYL DIMETHYL SULFONIUM IODIDE... 

Data have been reported for the reaction at 64 C between sodium ethoxide (A) and ethyl dimethyl sulfonium iodide CB] using ethanol as a solvent. 

Example. The reaction of sodium ethoxide, NaOC2H6, with ethyl dimethyl sulfonium iodide, (C2H6)(CH3)2SI, in absolute ethanol solution has been shown to lead to the following products ... 

In Table IV.7 this method is applied analytically to the data on the solvolysis of dimethyl ethyl sulfonium iodide by sodium ethoxide given originally in Tabic IV.2. 

SYNS OXYSONIUM IODIDE Q SULFONIUM, (2-((CYCLOHEXYLHYDROXYPHENYLACETYL)OXY)ETHY L)DIMETHYL-, IODIDE SULFONIUM, (2-HYDROXY-ETHYL)DIMETHYL-, IODIDE, a-PHENYLCYCLO-HEXANEGLYCOLATE... 

Electrophilic attack on the sulfur atom of thiiranes by alkyl halides does not give thiiranium salts but rather products derived from attack of the halide ion on the intermediate cyclic salt (B-81MI50602). Treatment of ds-2,3-dimethyl thiirane with methyl iodide yields cis-2-butene by two possible mechanisms (Scheme 31). A stereoselective isomerization of alkenes is accomplished by conversion to a thiirane of opposite stereochemistry followed by desulfurization by methyl iodide (75TL2709). Treatment of thiiranes with alkyl chlorides and bromides gives 2-chloro- or 2-bromo-ethyl sulfides (Scheme 32). Intramolecular alkylation of the sulfur atom of a thiirane may occur if the geometry is favorable the intermediate sulfonium ions are unstable to nucleophilic attack and rearrangement may occur (Scheme 33). 

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