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J Org Chem ; 80(10): 5196-209, 2015 May 15.
Article in English | MEDLINE | ID: mdl-25893894

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.


Subject(s)
Carbon Radioisotopes/chemistry , Cyclopropanes/chemistry , Furans/chemical synthesis , Platinum Compounds/chemistry , Platinum Compounds/chemical synthesis , Spiro Compounds/chemistry , Catalysis , Furans/chemistry , Oxidation-Reduction
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