title: Mechanistic investigation of the selective reduction of Meldrum's acids to β-hydroxy acids using SmI2 and H2O.
abstract: The mechanism of a recently reported first mono-reduction of cyclic 1,3-diesters (Meldrum's acids) to β-hydroxy acids with SmI2-H2O has been studied using a combination of reactivity, deuteration, kinetic isotope and radical clock experiments. Most crucially, the data indicate that the reaction proceeds via reversible electron transfer and that water, as a ligand for SmI2, stabilizes the radical anion intermediate rather than only promoting the first electron transfer as originally proposed.
authors.affiliation: School of Chemistry, The University of Manchester, Oxford Road, Manchester, M13 9PL, UK. michal.szostak@manchester.ac.uk david.j.procter@manchester.ac.uk.
authors.forename: Michal
authors.initials: M
authors.lastname: Szostak
authors.forename: Sarah E
authors.initials: SE
authors.lastname: Lyons
authors.forename: Malcolm
authors.initials: M
authors.lastname: Spain
authors.forename: David J
authors.initials: DJ
authors.lastname: Procter
mesh_terms: D003903:Deuterium / Q000737:chemistry; D004146:Dioxanes / Q000737:chemistry*; D004579:Electron Transport; D006880:Hydroxy Acids / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry; D007700:Kinetics; D010084:Oxidation-Reduction; D012493:Samarium / Q000737:chemistry*; D014867:Water / Q000737:chemistry
chemical_list: D004146:Dioxanes; D006880:Hydroxy Acids; D007454:Iodides; D014867:Water; D012493:Samarium; D003903:Deuterium; C076489:Meldrum's acid