1-Phenyl-3,4:5,6-dibenzocycloheptatrienyl anion. A stable antiaromatic carbanion
Journal Article
·
· J. Org. Chem.; (United States)
This article describes the photochemical study of carbanions with the synthesis of 1,2,3-triphenylpropene and its cyclic analogue, 1-phenyl-3,4:5,6-dibenzocycloheptatriene. This synthesis allowed for the investigation of not only paratropic effects but also the potential destabilization induced by cyclization of an eight electron system. Results frm NMR spectroscopy revealed the presence of large upfield proton shifts in the presence of downfield carbon shifts for the cyclic as compared to acyclic anion presenting evidence that the 1-phenyl-3,4:5,6-dibenzocycloheptatrienyl anion is a carbocyclic antiaromatic species.
- Research Organization:
- Univ. of Kentucky, Lexington
- OSTI ID:
- 6163891
- Journal Information:
- J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 47:24; ISSN JOCEA
- Country of Publication:
- United States
- Language:
- English
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
400500* -- Photochemistry
ANIONS
CHARGED PARTICLES
CHEMICAL PREPARATION
CHEMICAL PROPERTIES
CHEMICAL REACTIONS
HETEROCYCLIC OXYGEN COMPOUNDS
IONS
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PHOTOCHEMICAL REACTIONS
SPECTRA
STABILITY
SYNTHESIS
400301 -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
400500* -- Photochemistry
ANIONS
CHARGED PARTICLES
CHEMICAL PREPARATION
CHEMICAL PROPERTIES
CHEMICAL REACTIONS
HETEROCYCLIC OXYGEN COMPOUNDS
IONS
NMR SPECTRA
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PHOTOCHEMICAL REACTIONS
SPECTRA
STABILITY
SYNTHESIS