Detection of the 1,2-Didehydronaphthalene to 1H-Indenylidenecarbene Rearrangement by Intramolecular Trapping in a Flash Vacuum Pyrolytic Reaction

Abstract

Flash vacuum pyrolysis of 9-methyl-1,3-dihydronaphtho[1,2-c]furan-1,3-dione (8) at 750-880º gave exclusively 1H-cyclopent[ cd ]indene (9) and of 8-methyl-1,2-dihydrocyclobuta[a]naphthalene-1.2-dione (10) at 600-840º gave a mixture of (9) and acenaphthylene. Acenaphthylen-4-ol (12) was synthesized and found to be stable to flash vacuum pyrolysis over thetemperature range 600-900º.

These findings are discussed in relation to the rearrangement described in the title.