title: Evidence that Additions of Grignard Reagents to Aliphatic Aldehydes Do Not Involve Single-Electron-Transfer Processes.
abstract: Addition of allylmagnesium reagents to an aliphatic aldehyde bearing a radical clock gave only addition products and no evidence of ring-opened products that would suggest single-electron-transfer reactions. The analogous Barbier reaction also did not provide evidence for a single-electron-transfer mechanism in the addition step. Other Grignard reagents (methyl-, vinyl-, t-Bu-, and triphenylmethylmagnesium halides) also do not appear to add to an alkyl aldehyde by a single-electron-transfer mechanism.
authors.affiliation: Department of Chemistry, New York University, New York, New York 10003, United States.
authors.forename: Douglas A L
authors.initials: DA
authors.lastname: Otte
authors.affiliation: Department of Chemistry, New York University, New York, New York 10003, United States.
authors.forename: K A
authors.initials: KA
authors.lastname: Woerpel
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D004579:Electron Transport; D007202:Indicators and Reagents / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure
chemical_list: D000447:Aldehydes; D007202:Indicators and Reagents