title: Synthesis of highly substituted adamantanones from bicyclo[3.3.1]nonanes.
abstract: Trifluoromethanesulfonic acid and other electrophiles promote formation of the adamantanone core from the readily accessible 1,5-dimethyl-3,7-dimethylenebicyclo[3.3.1]nonan-9-one 2. Because adamantyl cation 3 can be trapped by a range of nucleophiles, including aromatic and heteroaromatic rings, alcohol, nitriles, and halides, access to a wide variety of functionality at the newly formed tertiary position is provided.
authors.affiliation: Department of Chemistry and Biochemistry, University of California , Los Angeles, California 90095-1569, United States.
authors.forename: Michael E
authors.initials: ME
authors.lastname: Jung
authors.forename: Gloria S
authors.initials: GS
authors.lastname: Lee
mesh_terms: D000218:Adamantane / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D008698:Mesylates / Q000737:chemistry*; D015394:Molecular Structure
chemical_list: C000596078:1,5-dimethyl-3,7-dimethylenebicyclo(3.3.1)nonan-9-one; D001643:Bridged Bicyclo Compounds; D008698:Mesylates; C012077:trifluoromethanesulfonic acid; D000218:Adamantane; C001862:adamantanone