Dithiocarboxylation of CH‐Acidic Sulfoxides and Thioethers
Reaction of (arylsulfinyl)acetonitriles or (arylthio)acetonitriles 1 (X = SO, S) with carbon disulfide in the presence of sodium hydride and subsequent alkylation yield the open‐chain or cyclic ketene S,S‐acetals 3 or 4, respectively. Using two equivalents of an α‐CH‐acidic halo compound as alkylating agent, thiophenes 5 are formed. Treatment of 3a with 2‐mercaptoethanol affords the 1,3‐oxathiolane 6. The 1H‐NMR spectra of phenylsulfinyl‐substituted compounds 3b, 4a, 4b, 5a and 6 show a typical AB system for the methylene group caused by the chiral sulfoxide group.
Thiocarbamoylation of CH‐Acidic Arylsulfinyl and Arylthio Compounds
Reaction of arylsulfinyl and arylthio acetonitriles (1) with phenyl isothiocyanate in the presence of sodium hydride and subsequent alkylation lead to the ketene S,N‐acetals (3a–h). Using methyl bromoacetate as alkylating agent thiazolidones (4a–c) are formed whereas phenacylbromide gives the 4‐hydroxythiazolidines (5a‐f). In an analogous way arylthio and arylsulfinyl acetophenones (6) react with phenyl isothiocyanate yielding S,N‐acetals (7a–e).
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ChemInform is a weekly Abstracting Service, delivering concise information at a glance that was extracted from about 100 leading journals. To access a ChemInform Abstract of an article which was published elsewhere, please select a “Full Text” option. The original article is trackable via the “References” option.
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