Some transformations of alkyl α-furfuryl sulfoxides
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.