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

Article abstract of DOI:10.1016/S0022-1139(00)82368-4

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<3.3.1.0^2,7>non-3-en-6-one (11) (by a <2 + 2> addition) and 1,2,7-trifluoro-3,4-(tetrafluorobenzo)tricyclo<3.3.1.0^2,7>non-3-en-8-one (12) (via an initial <3,5> photochemically-allowed sigmatropic shift).Pyrolysis of (9) at 455 deg C also gave (11), while at 490 deg C, both (9) and (11) gave 1-fluorovinyl 4,5,6,7,8-pentafluoro-1-naphthyl ketone (19).