STUDY OF THE PYROLYTIC CHEMISTRY OF ISOBENZOFURYLMETHYL BENZOATES

Pyrolysis of(1-isobenzofuryl)methyl benzoate (9a), produced in situ fr om flash vacuum pyrolysis of (7-oxa-1-benzonorbornenyl)methyl benzoate (10a), Save methylenebenzocyclobutenone (4), 2-ethynylbenzaldehyde (5 ) and benzocyclopentadienone (6). The deuterium-labeled study indicate d that the mechanism for die formation of these products involved the double migrations of benzoate group in 9a. Pyrolysis of (3-methyl-1-is obenzofuryl)methyl benzoate (9c) Save 1,3-dimethylene-1,3-dihydroisobe nzofuran (33), which is stable in benzene and hydrolyzed rapidly in ch loroform to give 1,2-diacetylbenzene (35). (C) 1997 Elsevier Science L td.