I. Mechanism of the formation of methylenecyclobutenone by the flash vacuum pyrolysis of ufrfuryl benzoate. II. Chemistry of 2-methylenebenzocyclobutenone and indenone prepared by the flash vacuum pyrolysis of 3-benzoyloxymethylbenzofuran

Technical Report · Fri Jun 01 00:00:00 EDT 1984

OSTI ID:6174227

Amah, A N

The flash vacuum pyrolysis chemistry of a series of deuterated furfuryl benzoates, furfuryl-..cap alpha.., ..cap alpha..-d/sub 2/ benzoate, furfuryl-5-d/sub 1/ benzoate, and furfuryl-3-d/sub 1/ benzoate have been investigated. Mechanisms were proposed for the formation of the pyrolysis products, methylenecyclobutenone, vinylacetylene, and the dimer of cyclopentadienone, from each of the compounds studies which involved initial alpha elimination of benzoic acid, a single (3,3) migration followed by alpha elimination of benzoic acid, and two (3,3) migrtions followed by alpha elimination of benzoic acid. Synthesis of 2-methylenebenzocyclobutenone and indenone by the flash vacuum pyrolysis of 3-benzoyloxymethylbenzofuran is described. A procedure was developed for the decarboxylation of 2,3-benzofurandicarboxylic acid in > 80% yield to the key intermediate 3-benzofurancarboxylic acid. Mechanisms were proposed for the formation of the pyrolysis products 2-methylenebenzocyclobutenone, indenone, phenylacetylene, and o-ethynylbenzaldehyde.

• Research Organization: Ames Lab., IA (USA)
• DOE Contract Number: W-7405-ENG-82
• OSTI ID: 6174227
• Report Number(s): IS-T-1105; ON: DE85007088
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
AROMATICS
BENZOFURANS
BENZOIC ACID
CARBOXYLIC ACIDS
CHEMICAL REACTIONS
DECOMPOSITION
DEUTERATION
FURANS
HETEROCYCLIC COMPOUNDS
KETONES
MONOCARBOXYLIC ACIDS
ORGANIC ACIDS
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
PYROLYSIS
SYNTHESIS
THERMOCHEMICAL PROCESSES