Extreme oxatriquinanes: Structural characterization of α-oxyoxonium species with extraordinarily long carbon-oxygen bonds

Gorkem Gunbas, William L. Sheppard, James C. Fettinger, Marilyn M. Olmstead, Mark Mascal

Research output: Contribution to journalArticle

10 Scopus citations

Abstract

The first stable α-oxyoxonium species have been synthesized and characterized. Strong donation of nonbonding electrons on oxygen into the adjacent σ(C-O+) orbital was predicted by modeling to result in unheard of carbon-oxygen bond lengths. The kinetic stability of the triquinane ring system provides a platform upon which to study these otherwise elusive species, which are evocative of intermediates on the acetalization reaction pathway. Crystallographic analysis of the α-hydroxy and α-methoxy oxatriquinane triflates reveals 1.658 and 1.619 Å C-O+ bond lengths, respectively, the former of which is a new record for the C-O bond.

Original languageEnglish (US)
Pages (from-to)8173-8176
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number22
DOIs
StatePublished - Jun 5 2013

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ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

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