Room-temperature alternative to the Arbuzov reaction: the reductive deoxygenation of acyl phosphonates.
The reductive deoxygenation of acyl phosphonates using a Wolff-Kishner-like sequence is described. This transformation allows direct access to alkyl phosphonates from acyl phosphonates at room temperature. The method can be combined with acyl phosphonate synthesis into a one pot, four-step procedure for the conversion of carboxylic acids into alkyl phosphonates. The methodology works well for a variety of aliphatic acids and shows a functional group tolerance similar to that of other hydrazone-forming reactions.
Kedrowski
Sean M A
SM
Division of Chemistry and Chemical Engineering, California Institute of Technology, Pasadena, California 91125, USA.
Dougherty
Dennis A
DA
D000215:Acylation; D006834:Hydrazines / Q000737:chemistry; D015394:Molecular Structure; D063065:Organophosphonates / Q000737:chemistry*; D010084:Oxidation-Reduction; D013696:Temperature
D006834:Hydrazines; D063065:Organophosphonates; C029424:hydrazine