Skip to main content
OSTI.GOVU.S. Department of Energy Office of Scientific and Technical Information
U.S. Department of Energy
Office of Scientific and Technical Information
 

Chemistry of 2,3-dimethylene-2,3-dihydrofurans and other reactive olefins prepared by the flash vacuum pyrolysis of substituted furylmethyl esters

Technical Report ·
OSTI ID:5812615
The flash vacuum pyrolysis chemistry of a series of methyl-substituted, furfuryl benzoates and methyl-substituted, 3-furylmethyl benzoates has been investigated. Mechanisms were proposed for the formation of the pyrolysis products, from each of the compounds studied, which involved either ..cap alpha.. or ..beta.. eliminations of benzoic acid after one or more (3,3) sigmatropic shifts of the benzoate group. These reactions provide a method for the preparation of the bis(methylene)-dihydrofurans which are the furan analogs of the ortho- and para-quinodimethanes, an actively investigated group of reactive intermediates. The chemical reactions of the 2,3-bis(methylene)-2,3-dihydrofurans, which were investigated in this study, included thermal dimerization reactions, Diels-Alder reactions and chelatropic reactions with sulfur dioxide. Pyrolysis of diesters of 3,4-bis(hydroxymethyl)-2,5-dimethylfuran formed furanoradialene as the only major, nonpolymeric product. Warming the product solutions to room temperature converted furanoradialene into one (4+2) dimer. Several approaches toward the synthesis of (2.2.2.2.)-(2,3,4,5)furanophane were investigated. The failure to produce the desired furanophane was attributed to a retro(4+4) reaction which occurred during the pyrolysis of 4,4'-bis(acetoxymethyl)-5,5'-dimethyl-(2,2)(2,3)furanophane. 277 references, 15 figures, 6 tables.
Research Organization:
Ames Lab., IA (USA)
DOE Contract Number:
W-7405-ENG-82
OSTI ID:
5812615
Report Number(s):
IS-T-1001; ON: DE85009226
Country of Publication:
United States
Language:
English

Similar Records

I. Kinetic and mechanistic study of the (4+4) dimerization of 2,3-dimethylene-2,3-dihydrofuran. II. Preparation of 2,3-dimethylene-2,3-dihydrogenzo(b)furan by the flash vacuum pyrolysis of 2-methyl-3-benzo(b)furylmethyl benzoate. III. Reaction of 2,3-dimethylene-2,3-dihydrofuran with triplet oxygen
Technical Report · Thu Feb 28 23:00:00 EST 1985 · OSTI ID:5949736
I. Kinetic and mechanistic study of the (4+4) dimerization of 2,3-dimethylene-2,3-dihydrofuran. II. Preparation of 2,3-dimethylene-2,3-dihydrobenzo(B)furan by the flash vacuum pyrolysis of 2-methyl-3-benzo(B)furylmethyl benzoate. III. Reaction of 2,3-dimethylene-2,3-dihydrofuran with triplet oxygen
Thesis/Dissertation · Mon Dec 31 23:00:00 EST 1984 · OSTI ID:6036372
Preparation of 2,3-dimethylene-2,3-dihydrofurans by the flash vacuum pyrolysis of substituted furylmethyl esters
Journal Article · Tue Nov 03 23:00:00 EST 1981 · J. Am. Chem. Soc.; (United States) · OSTI ID:5637975

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
ALDEHYDES
ALKANES
ALKENES
AROMATICS
BENZENE
BENZOFURANS
CHALCOGENIDES
CHEMICAL PREPARATION
CHEMICAL REACTION KINETICS
CHEMICAL REACTIONS
CHROMATOGRAPHY
CYCLOALKENES
DATA
DECOMPOSITION
DIELS-ALDER REACTION
DIMERIZATION
ESTERS
EXPERIMENTAL DATA
FURANS
FURFURAL
GAS CHROMATOGRAPHY
HETEROCYCLIC COMPOUNDS
HIGH TEMPERATURE
HIGH VACUUM
HYDROCARBONS
INFORMATION
INFRARED SPECTRA
KINETICS
MAGNETIC RESONANCE
METHANE
NUCLEAR MAGNETIC RESONANCE
NUMERICAL DATA
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
OXIDES
OXYGEN COMPOUNDS
POLYMERIZATION
PYROLYSIS
PYROLYSIS PRODUCTS
QUINONES
REACTION KINETICS
RESONANCE
SEPARATION PROCESSES
SPECTRA
SULFUR COMPOUNDS
SULFUR DIOXIDE
SULFUR OXIDES
SYNTHESIS
THEORETICAL DATA
THERMOCHEMICAL PROCESSES