title: Grignard-mediated reduction of 2,2,2-trichloro-1-arylethanones.
abstract: 2,2,2-Trichloro-1-aryl-ethanones can be reduced by RMgX to the corresponding 2,2-dichloro-1-arylethen-1-olates and trapped with a range of electrophiles resulting in either reduction, reduction/aldol, reduction/Claisen condensation or reduction/aldol-Tishchenko products. In addition we demonstrate that 2,2-dichloro-1-arylethen-1-olates undergo counter-ion controlled Darzens condensations, which can be followed by a thermal rearrangement as a route to 1,3-diaryl-3-chloropropane-1,2-diones.
authors.affiliation: School of Chemistry, Bedson Building, Newcastle University, Newcastle upon Tyne, NE1 7RU, UK. Michael.Hall@newcastle.ac.uk.
authors.forename: Ali H
authors.initials: AH
authors.lastname: Essa
authors.forename: Reinner I
authors.initials: RI
authors.lastname: Lerrick
authors.forename: Eçe
authors.initials: E
authors.lastname: Çiftçi
authors.forename: Ross W
authors.initials: RW
authors.lastname: Harrington
authors.forename: Paul G
authors.initials: PG
authors.lastname: Waddell
authors.forename: William
authors.initials: W
authors.lastname: Clegg
authors.forename: Michael J
authors.initials: MJ
authors.lastname: Hall
mesh_terms: D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D004980:Ethane / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D006843:Hydrocarbons, Chlorinated; C116609:3-hydroxybutanal; D004980:Ethane