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

Gerald M. Brooke, Ian Eggleston, Francis I. Hale

Research output: Contribution to journalArticle

Abstract

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.
Original languageEnglish
Pages (from-to)421
Number of pages434
JournalJournal of Fluorine Chemistry
Volume38
Issue number3
DOIs
Publication statusPublished - 1988

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