19F NMR spectroscopy of polyhalonaphthalenes: Part V. Halex reactions of polychloroisoquinolines

Nucleophilic fluoride fluoro-dechlorination of four isoquinolines (5,6,7,8-tetrachloro-,3,5,6,7,8-pentachloro-,3,4,5,6,7,8-hexachloro- and 1,3,4,5,6,7,8-heptachloro-isoquinoline) led to the preparation of 15 new polychloropolyfluoro isoquinolines by reaction with caesium fluoride in DMSO at 100°C. The product from the perchloroisoquinoline was an inseparable mixture of C9Cl7−nFnN where n is 1–3. The order of reactivity in 1,3,4,5,6,7,8-heptachloro-isoquinoline [10] to nucleophilic attack by fluoride was 1⪢6=7=8>3=5>4