Gas-phase intramolecular Diels-Alder reactions of 2,3-dimethylene-2,3-dihydrofurans; Formation of 9-methylanthracene and anthracene by pyrolysis; and preparation of cyclopentadienones by flash vacuum pyrolysis

Technical Report · Mon Jun 01 00:00:00 EDT 1987

OSTI ID:6478303

Lee, S K

The intramolecular Diels-Alder reactions of 2,3-dimethylene-2,3-dihydrofurans have been investigated through the pyrolysis of 2-alkenyl-3-furylmethyl benzoates. Under FVP conditions each of the 2,3-dimethylene-2,3-hydrofurans can undergo an intramolecular Diels-Alder reaction or 1,5-hydrogen shift to give the corresponding tricyclics 4c,t, 5c,t, and 6c,t and 1,5-hydrogen shift products 36c,t and 37c,t. FVP of 1,5-dibenzocyclooctadienes containing heteroatoms and dibenzosuberanes gave the corresponding tricyclic compounds (benzodifuran, acridine, and anthracene) except 6H,11H-dibenzo(b,f) (1,4)-dioxocin. FVP of the latter gave (2-hydroxybenzyl)-o-benzaldehyde as a major product. A mechanistic study of the regiospecific formation of 9-methylanthracene from the sealed tube pyrolysis the (4 + 4) dimer of o-xylylene is presented. A new method of preparing cyclopentadienones by the pyrolysis of cyclic diethers is presented. Cyclopentadienones including inden-2-one have been utilized in the synthesis of polycyclic compounds.

• Research Organization: Ames Lab., IA (USA)
• DOE Contract Number: W-7405-ENG-82
• OSTI ID: 6478303
• Report Number(s): IS-T-1293; ON: DE87011255
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400201* -- Chemical & Physicochemical Properties
ANTHRACENE
AROMATICS
CHEMICAL PREPARATION
CHEMICAL REACTION YIELD
CHEMICAL REACTIONS
CONDENSED AROMATICS
DECOMPOSITION
DIELS-ALDER REACTION
DIMERS
FLUIDS
FURANS
GASES
HETEROCYCLIC COMPOUNDS
HYDROCARBONS
KETONES
ORGANIC COMPOUNDS
ORGANIC OXYGEN COMPOUNDS
POLYCYCLIC AROMATIC HYDROCARBONS
PYROLYSIS
SYNTHESIS
THERMOCHEMICAL PROCESSES
YIELDS