ISSN:
0170-2041
Keywords:
Sulfoxides
;
Ketene S,S-acetals
;
Thiophenes
;
Chemistry
;
Organic Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
Notes:
Dithiocarboxylation of CH-Acidic Sulfoxides and ThioethersReaction 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.
Additional Material:
1 Tab.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/jlac.199219920169
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