Pt-Catalyzed Rearrangement of Oxaspirohexanes to 3-Methylenetetrahydrofurans: Scope and Mechanism

Christian A. Malapit, Sampada M. Chitale, Meena S. Thakur, Rosa Taboada, Amy R. Howell*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

19 Scopus citations


A novel Pt-catalyzed rearrangement of oxaspirohexanes to 3-methylenetetrahydrofurans is reported. Mechanistic studies by 13C-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. (Chemical Equation Presented).

Original languageEnglish (US)
Pages (from-to)5196-5209
Number of pages14
JournalJournal of Organic Chemistry
Issue number10
StatePublished - May 15 2015
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry


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