Tetrahedron p. 17115 - 17126 (1997)
Update date:2022-08-04
Topics:
Chen, Ping-Shu
Chou, Chin-Hsing
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).
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