title: Direct conversion of benzylic and allylic alcohols to phosphonates.
abstract: Benzyl phosphonate esters often serve as reagents in Horner-Wadsworth-Emmons reactions. In most cases, they can be prepared from benzylic alcohols via formation of the corresponding halide followed by an Arbuzov reaction. To identify a more direct synthesis of phosphonate esters, we have developed a one-flask procedure for conversion of benzylic and allylic alcohols to the corresponding phosphonates through treatment with triethyl phosphite and ZnI(2).
authors.affiliation: Department of Chemistry, University of Iowa, Iowa City, Iowa 52242-1294, United States.
authors.forename: Rocky J
authors.initials: RJ
authors.lastname: Barney
authors.forename: Rebekah M
authors.initials: RM
authors.lastname: Richardson
authors.forename: David F
authors.initials: DF
authors.lastname: Wiemer
mesh_terms: D019905:Benzyl Alcohol / Q000737:chemistry; D002384:Catalysis; D002712:Chlorides / Q000737:chemistry; D004952:Esters / Q000737:chemistry; D015394:Molecular Structure; D063065:Organophosphonates / Q000138:chemical synthesis*; D017905:Phosphites / Q000737:chemistry; D020005:Propanols / Q000737:chemistry; D013237:Stereoisomerism; D013267:Stilbenes / Q000138:chemical synthesis*; D017967:Zinc Compounds / Q000737:chemistry
chemical_list: D002712:Chlorides; D004952:Esters; D063065:Organophosphonates; D017905:Phosphites; D020005:Propanols; D013267:Stilbenes; D017967:Zinc Compounds; C006463:allyl alcohol; C018680:triethyl phosphite; C016837:zinc chloride; D019905:Benzyl Alcohol