Sodium allyl oxide reacted with 2,3,4,5,6,7,8-heptafluoroquinoline to give allyl 3,4,5,6,7,8-hexafluoroquinolin-2-yl ether (7) and allyl 2,3,5,6,7,8-hexafluoroquinolin-4-yl ether (8) in the ratio 3.4:1 respectively, and with 1,3,4,5,6,7,8-heptafluoroisoquinoline to give allyl 3,4,5,6,7,8-hexafluoroisoquinolin- 1- yl ether (9). Thermolyses of (7) and (9) in tetralin at 212°C gave the Claisen rearrangement products (10) and (12) in which nitrogen is the migration terminus, in slow reactions over 48 h, whereas the isomerisation of (8) to (11) in which carbon is the migration terminus, was complete within 2.5 h at 147.5°C. Compound (11) is very susceptible to hydrolysis, giving with undried toluene, the dione (13) containing half a molecule of solvent toluene.
Brooke, G. M., Eggleston, I., & Hale, F. I. (1988). The preparation and thermolysis reactions of allyl 3,4,5,6,7,8- hexafluoroquinolin-2-yl ether, allyl 2,3,5,6,7,8- hexafluoroquinolin-4-yl ether and allyl 3,4,5,6,7,8- hexafluoroisoquinolin-1-yl ether. Journal of Fluorine Chemistry, 38(3), 421. https://doi.org/10.1016/S0022-1139(00)81077-5