The preparation and reactions of 1,3,4,5,6,7,8-heptafluoro-2-naphthyl prop-2-enyl ether: Formation of 1,3,4,5,6,7,8-heptafluoro-1-(prop-2-enyl)naphthalen-2-one and the photolysis and pyrolysis of this ketone [1].

1,3,4,5,6,7,8-Heptafluoro-2-naphthyl prop-2-enyl ether (8) was isomerised in boiling xylene to 1,3,4,5,6,7,8-heptafluoro- 1-(prop-2-enyl)naphthalen-2-one (9). Photolysis of (9) gave 2,5,7-trifluoro-3,4-(tetrafluorobenzo)tricyclo[3.3.1.O^2,7]non-3- en-6-one (11) (by a [2 + 2] addition) and 1,2,7-trifluoro-3,4- (tetrafluorobenzo) tricyclo [3.3.1.O^2,7]non-3-en-8-one (12) (via an initial [3,5] photochemically-allowed sigmatropic shift). Pyrolysis of (9) at 455° also gave (11), while at 490°, both (9) and (11) gave 1-fluorovinyl 4,5,6,7,8-pentafluoro-1-naphthyl ketone (19).     

Partially fluorinated heterocyclic compounds. Part 24. [1] A plausible mechanism for the formation of the fischer indole product from acetophenone 1,3,4,5,6,7,8-heptafluoro-2-naphthylhydrazone in which o-fluorine is lost

Acetophenone 1,3,4,5,6,7,8-heptafluoro-2-naphthylhydrazone (1) reacts in tetralin at reflux to give 4,5,6,7,8,9-hexafluoro-2-phenylbenz[e]indole (2) as the major product, accompanied by other materials including acetophenone 3,4,5,6,7,8-hexafluoro-2-naphthylhydrazone (4) which is proposed as the true precursor to the Fisher indole product (2) since it gives (2) under the same conditions. The presence of α-tetralone in the reaction mixture provides the clue to a reductive elimination of F^- from (1).