title: Aliphatic C-H activation with aluminium trichloride-acetyl chloride: expanding the scope of the Baddeley reaction for the functionalisation of saturated hydrocarbons.
abstract: The functionalisation of decalin by means of an "aliphatic Friedel-Crafts" reaction was reported over fifty years ago by Baddeley et al. This protocol is of current relevance in the context of C-H activation and here we demonstrate its applicability to a range of other saturated hydrocarbons. Structural elucidation of the products is described and a mechanistic rationale for their formation is presented. The "aliphatic Friedel-Crafts" procedure allows for production of novel oxygenated building blocks from abundant hydrocarbons and as such can be considered to add significant synthetic value in a single step.
authors.affiliation: Department of Chemistry, University of Bath, Bath, UK.
authors.forename: Catherine L
authors.initials: CL
authors.lastname: Lyall
authors.forename: Mario
authors.initials: M
authors.lastname: Uosis-Martin
authors.forename: John P
authors.initials: JP
authors.lastname: Lowe
authors.forename: Mary F
authors.initials: MF
authors.lastname: Mahon
authors.forename: G Dan
authors.initials: GD
authors.lastname: Pantoş
authors.forename: Simon E
authors.initials: SE
authors.lastname: Lewis
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000077410:Aluminum Chloride; D017607:Aluminum Compounds / Q000737:chemistry*; D002712:Chlorides / Q000737:chemistry*; D018360:Crystallography, X-Ray; D006838:Hydrocarbons / Q000138:chemical synthesis* / Q000737:chemistry; D008958:Models, Molecular; D015394:Molecular Structure; D011789:Quantum Theory
chemical_list: D000085:Acetates; D017607:Aluminum Compounds; D002712:Chlorides; D006838:Hydrocarbons; D000077410:Aluminum Chloride; C081124:acetyl chloride