Alkali metal enolates stable enolate equivalents

A number of experimental details have contributed to an understanding of the mechanism of reductions carried out under these conditions. Among the more important observations are the facts that ketones react with one and only one equivalent of alkali metal in NH3 enolizable ketones afford equal amounts of enolate and alcohol, while nonenolizable ketones give metal ketyls which are stable at low temperatuie. Also, pinacol formation is a major reaction path with Li, but K affords little or no pina-col. - Finally, a-deuterio ketones afford product alcohols in which deuterium has been transferred to the carbinol carbon of the product alcohol or alcohols. - ... 

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