Related Experiment Video
Updated: May 11, 2026
![Solid-phase Synthesis of [4.4] Spirocyclic Oximes](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F58508.jpg&w=3840&q=50)
Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Extreme oxatriquinanes: structural characterization of α-oxyoxonium species with extraordinarily long carbon-oxygen
Gorkem Gunbas1, William L Sheppard, James C Fettinger
1Department of Chemistry, University of California-Davis , 1 Shields Avenue, Davis, California 95616, United States.
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.
Related Concept Videos
Resonance
Oxidation of Phenols to Quinones
o-hydroxy phenols are oxidized to o-quinones and p-hydroxy phenols to p-quinones. Such redox reactions involve the transfer of two electrons and two protons. The reversible redox property is crucial in...
Lewis Structures of Molecular Compounds and Polyatomic Ions
Alkynes to Carboxylic Acids: Oxidative Cleavage
Aromatic Hydrocarbon Anions: Structural Overview
Due to the absence of continuous overlap of p...
Structure and Nomenclature of Epoxides

