title: Alkenylphosphonates: unexpected products from reactions of methyl 2-[(diethoxyphosphoryl)methyl]benzoate under Horner-Wadsworth-Emmons conditions.
abstract: Methyl 2-[(diethoxyphosphoryl)methyl]benzoate reacts with several aldehydes to produce an alkenylphosphonate as the major product, together with varying amounts of the expected Horner-Wadsworth-Emmons product, a 1,2-disubstituted E-alkene. Use of a bulky aldehyde or the tert-butyl ester favours the normal HWE product.
authors.affiliation: School of Chemical and Physical Sciences, Victoria University of Wellington, PO Box 600, Wellington 6140, New Zealand.
authors.forename: Lynton J
authors.initials: LJ
authors.lastname: Baird
authors.forename: Cédric
authors.initials: C
authors.lastname: Colomban
authors.forename: Claire
authors.initials: C
authors.lastname: Turner
authors.forename: Paul H
authors.initials: PH
authors.lastname: Teesdale-Spittle
authors.forename: Joanne E
authors.initials: JE
authors.lastname: Harvey
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D000475:Alkenes / Q000138:chemical synthesis*; D000838:Anions / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis*; D001565:Benzoates / Q000737:chemistry; D002625:Chemistry, Organic; D018942:Macrolides / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D063065:Organophosphonates / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D000475:Alkenes; D000838:Anions; D000900:Anti-Bacterial Agents; D001565:Benzoates; D018942:Macrolides; D063065:Organophosphonates; C452445:aigialomycin D