I. Gas-phase intramolecular Diels-Alder reactions of 2,3-dimethylene-2,3-dihydrofurans; II. Formation of anthracene and other polycyclic aromatic compounds in the pyrolysis of 1,5-dibenzocyclooctadienes and related compounds; III. Formation of 9-methylanthracene and anthracene in the pyrolysis of 5,6,11,12-tetrahydrodibenzo[a,e]cyclooctene and other related compounds; IV. Preparation of cyclopentadienones by flash vacuum pyrolysis and their dimerization and intramolecular reactions

Date
1987
Authors
Lee, Suk
Major Professor
Advisor
Committee Member
Journal Title
Journal ISSN
Volume Title
Publisher
Altmetrics
Authors
Research Projects
Organizational Units
Chemistry
Organizational Unit
Journal Issue
Series
Department
Chemistry
Abstract

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-dihydrofurans can undergo an intramolecular Diels-Alder reaction or 1,5-hydrogen shift to give the corresponding tricycles 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 (18), acridine (24), and anthracene with exception of 6H,11H-dibenzo b,f 1,4 -dioxocin (17). The FVP of 17 gave (2-hydroxybenzyl)-o-benzaldehyde (28) as a major product;A mechanistic study of the regiospecific formation of 9-methyl- anthracene from the sealed tube pyrolysis the 4+4 dimer of o-xylylene (1) is presented. This study was carried out by pyrolyzing several possible precursors for 9-methylanthracene (e.g., 5,6-dihydrodibenzo a,e cyclooctene, di-o-tolylethane, and 5-methyl- dibenzosuberane). Sealed tube pyrolyses of dibenzosuberanes and dibenzosuberones were also carried out;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;The transient existence of these intermediates has also been proven by the isolation of polycyclic compounds; *DOE Report IS-T-1293. This work was performed under contract No. W-7405-Eng-82 with the U.S. Department of Energy.

Comments
Description
Keywords
Citation
Source