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Chemistry of Heterocyclic Compounds

, Volume 7, Issue 7, pp 849–853 | Cite as

Some transformations of alkyl α-furfuryl sulfoxides

  • Ya. L. Gol'dfarb
  • A. P. Y'akubov
  • L. N. Belen'kii
Article
  • 39 Downloads

Abstract

Under the influence of sodium or potassium methoxide, alkyl α-furfuryl sulfoxides are converted, through removal of a proton from the methylene group of the furfuryl residue, to the corresponding cartbanions which, by reacting with methyl benzoate, form β -keto sulfoxides. The latter are cleaved to phenyl α-furfuryl ketone by the action of amalgamated aluminum. In the case of α-furfuryl α-thienyl sulfoxide, nucleophilic attack is directed nonselectively to one of the methylene groups. This method opens up the possibility for the synthesis of hard-to-obtain, unsymmetrical ketones in which one of the radicals is an aryl (hetaryl) grouping, and the other is a benzyl group or its heterocyclic analog.

Keywords

Sodium Aluminum Methylene Potassium Organic Chemistry 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.

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Copyright information

© Consultants Bureau, a division of Plenum Publishing Corporation 1974

Authors and Affiliations

  • Ya. L. Gol'dfarb
    • 1
  • A. P. Y'akubov
    • 1
  • L. N. Belen'kii
    • 1
  1. 1.N. D. Zelinskii Institute of Organic ChemistryAcademy of Sciences of the USSRMoscow

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