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


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.


Sodium Aluminum Methylene Potassium Organic Chemistry 
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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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