Study of the pyrolytic chemistry of isobenzofurylmethyl benzoates

Pyrolysis of (1-isobenzofuryl)methyl benzoate ( 9a), produced in situ from flash vacuum pyrolysis of (7-oxa-1-benzonorbornenyl)methyl benzoate ( 10a), gave methylenebenzocyclobutenone ( 4), 2-ethynylbenzaldehyde ( 5) and benzocyclopentadienone ( 6). The deuterium-labeled study indicated that the mec...

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Bibliographic Details
Published in:Tetrahedron 1997-12, Vol.53 (50), p.17115-17126
Main Authors: Chen, Ping-Shu, Chou, Chin-Hsing
Format: Article
Language:English
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Summary:Pyrolysis of (1-isobenzofuryl)methyl benzoate ( 9a), produced in situ from flash vacuum pyrolysis of (7-oxa-1-benzonorbornenyl)methyl benzoate ( 10a), gave methylenebenzocyclobutenone ( 4), 2-ethynylbenzaldehyde ( 5) and benzocyclopentadienone ( 6). The deuterium-labeled study indicated that the mechanism for the formation of these products involved the double migrations of benzoate group in 9a. Pyrolysis of (3-methyl-1-isobenzofuryl)methyl benzoate ( 9c) gave 1,3-dimethylene-1,3-dihydroisobenzofuran ( 33), which is stable in benzene and hydrolyzed rapidly in chloroform to give 1,2-diacetylbenzene ( 35). Graphic
ISSN:0040-4020
1464-5416
DOI:10.1016/S0040-4020(97)10134-X