Study of the pyrolytic chemistry of isobenzofurylmethyl benzoates

Article abstract of DOI:10.1016/S0040-4020(97)10134-X

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).