Effects of [alpha]-methyl group substitution on the dimerization products of furan-based o-quinodimethanes
Journal Article
·
· Journal of the American Chemical Society; (United States)
- Iowa State Univ., Ames, IA (United States) Ames Lab., IA (United States)
3-Ethylidene-2-methylene-(12), 2-ethylidene-3-methylene-(13), and 2,3-diethylidene-(14)2,3-dihydrofurans were prepared by fluoride induced 1,4-conjugative elimination of trimethylsilyl acetate from the appropriate precursors. The [sup 1]H NMR spectra of these furan-based o-quinodimethanes were obtained and the dimerization products of each were studied. It was found that a methyl group at the 3-methylene position retards the rate of dimerization which is consistent with the previously proposed dimerization mechanism, the two-step mechanism involving rate-determining formation of a diradical intermediate followed by rapid cyclization of the diradical. 25 refs., 8 figs., 6 tabs.
- DOE Contract Number:
- W-7405-ENG-82
- OSTI ID:
- 6493254
- Journal Information:
- Journal of the American Chemical Society; (United States), Journal Name: Journal of the American Chemical Society; (United States) Vol. 117:3; ISSN JACSAT; ISSN 0002-7863
- Country of Publication:
- United States
- Language:
- English
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OSTI ID:5638167
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Related Subjects
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400100* -- Analytical & Separations Chemistry
400201 -- Chemical & Physicochemical Properties
664100 -- Theory of Electronic Structure of Atoms & Molecules-- (1992-)
664200 -- Spectra of Atoms & Molecules & their Interactions with Photons-- (1992-)
74 ATOMIC AND MOLECULAR PHYSICS
ALKYL RADICALS
CHEMICAL REACTIONS
CHEMISTRY
CYCLIZATION
DATA
DIMERIZATION
EXPERIMENTAL DATA
FURANS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
INFORMATION
MAGNETIC RESONANCE
METHYL RADICALS
MOLECULAR STRUCTURE
NUCLEAR MAGNETIC RESONANCE
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
POLYMERIZATION
PROTON SPECTRA
RADICALS
RESONANCE
SPECTRA
400100* -- Analytical & Separations Chemistry
400201 -- Chemical & Physicochemical Properties
664100 -- Theory of Electronic Structure of Atoms & Molecules-- (1992-)
664200 -- Spectra of Atoms & Molecules & their Interactions with Photons-- (1992-)
74 ATOMIC AND MOLECULAR PHYSICS
ALKYL RADICALS
CHEMICAL REACTIONS
CHEMISTRY
CYCLIZATION
DATA
DIMERIZATION
EXPERIMENTAL DATA
FURANS
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
INFORMATION
MAGNETIC RESONANCE
METHYL RADICALS
MOLECULAR STRUCTURE
NUCLEAR MAGNETIC RESONANCE
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
POLYMERIZATION
PROTON SPECTRA
RADICALS
RESONANCE
SPECTRA