title: Pt-catalyzed rearrangement of oxaspirohexanes to 3-methylenetetrahydrofurans: scope and mechanism.
abstract: A novel Pt-catalyzed rearrangement of oxaspirohexanes to 3-methylenetetrahydrofurans is reported. Mechanistic studies by (13)C-labeling experiments confirm oxidative addition of Pt(II) regioselectively to the least substituted carbon-carbon bond of the cyclopropane to form a platinacyclobutane intermediate. To our knowledge, this is the first alkoxy-substituted platinacyclobutane that has been observed spectroscopically. The scope and a proposed mechanism of this new Pt-catalyzed transformation are described.
authors.affiliation: Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States.
authors.forename: Christian A
authors.initials: CA
authors.lastname: Malapit
authors.affiliation: Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States.
authors.forename: Sampada M
authors.initials: SM
authors.lastname: Chitale
authors.affiliation: Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States.
authors.forename: Meena S
authors.initials: MS
authors.lastname: Thakur
authors.affiliation: Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States.
authors.forename: Rosa
authors.initials: R
authors.lastname: Taboada
authors.affiliation: Department of Chemistry, University of Connecticut, Storrs, Connecticut 06269-3060, United States.
authors.forename: Amy R
authors.initials: AR
authors.lastname: Howell
mesh_terms: D002250:Carbon Radioisotopes / Q000737:chemistry*; D002384:Catalysis; D003521:Cyclopropanes / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D010084:Oxidation-Reduction; D017671:Platinum Compounds / Q000138:chemical synthesis* / Q000737:chemistry*; D013141:Spiro Compounds / Q000737:chemistry*
chemical_list: D002250:Carbon Radioisotopes; D003521:Cyclopropanes; D005663:Furans; D017671:Platinum Compounds; D013141:Spiro Compounds; C030797:cyclopropane