title: One-pot synthesis of trichloromethyl carbinols from primary alcohols.
abstract: Versatile trichloromethyl carbinols can be prepared in one pot from primary alcohols by treatment with Dess-Martin periodinane (DMP) in CHCl(3) followed by introduction of commercially available 1,5,7-triazabicyclo[4.4.0]dec-5-ene (TBD). A modification of the method was used to convert chiral primary alcohol (R)-(-)-2,2-dimethyl-1,3-dioxolane-4-methanol to the corresponding trichloromethyl carbinol with complete stereochemical fidelity, despite the reactant proceeding through a base-sensitive aldehyde intermediate.
authors.affiliation: Department of Chemistry, The University of Alabama, P.O. Box 870336, Tuscaloosa, Alabama 35487-0336, United States.
authors.forename: Manoj K
authors.initials: MK
authors.lastname: Gupta
authors.forename: Zhexi
authors.initials: Z
authors.lastname: Li
authors.forename: Timothy S
authors.initials: TS
authors.lastname: Snowden
mesh_terms: D000438:Alcohols / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D004148:Dioxolanes / Q000737:chemistry*; D006843:Hydrocarbons, Chlorinated / Q000138:chemical synthesis* / Q000737:chemistry*; D000432:Methanol / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D000438:Alcohols; D000447:Aldehydes; D004148:Dioxolanes; D006843:Hydrocarbons, Chlorinated; C024356:2,2-dimethyl-1,3-dioxolane-4-methanol; D000432:Methanol