No abstract

Ethenesulphonyl chloride reacts with a mixture of a tertiary amine and an alcohol by SN2' attack of the amine to form the positively charged sulphene which then gives a mixture of the ethenesulphonate and 2-trialkylammonioethanesulphonate esters.THE formation of alkyl ethenesulphonates (2) by the reaction of ethenesulphonyl chloride (1) with alcohols in the presence of a tertiary amine is apparently unreported, even though compounds (2) are made under similar conditions from 2-chloroethanesulphonyl chloride,' which is also known to give (1) readily with 2,6-lutidine., A recent r e p ~r t , ~ in fact, claims 70--80~0 yields of the betaine (Py+CH,CH,SO,-) from (1) and pyridine (Py) in methanol or ethanol. We report on our work on the products and the mechanism of the reaction of (1) with tertiary aniines and alcohols. The reaction (in CH,Cl, a t 25 OC, for example) was found to occur very rapidly to give a mixture of esters

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The treatment of a variety of heterocyclic thiones with hydrogen peroxide in acetic acid produces either heteroaromatic cations or the corresponding "oxo" compound. The results may be correlated with structural and electronic features. Benzo substitution or the presence of strongly electron withdrawing groups in the molecule favors the latter product, whereas the presence of a σ trivalent nitrogen atom in the molecule favors the former.

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