90408-38-1

The vapour phase reaction of undecafluorocyclohexanecarbonitrile (1) with cobalt(III) or silver(II) fluoride caused stepwise saturation of the CN triple bond to give C6F11CF=NF and C6F11CF2NF2, whereas reaction in a sealed tube with silver(II) fluoride gave the azomethane C6F11CF2N=NCF2C6F11 and with silver(I) fluoride gave tris(undecafluorocyclohexyl)-s-triazine.Methylamine, isopropylamine, and dimethylamine with the nitrile (1) gave the corresponding amidines.Vapour phase fluorination of pentafluorobenzonitrile by cobalt(III) fluoride or potassium tetrafluorocobaltate(III) afforded the nitrile (1), together with nonafluorocyclohex-3-enecarbonitrile (4).The latter was oxidised by potassium permanganate to 3-cyanoheptafluorohexane-1,6-dioic acid.Nonafluorocyclohex-1-enecarbonitrile (2) underwent classical nucleophilic addition-elimination sequences with methanol and with sodium methoxide to give progressively octafluoro-2-methoxy-, heptafluoro-6,6-dimethoxy-, and hexafluoro-2,6,6-trimethoxy-cyclohex-1-enecarbonitrile, whilst with ammonia, 2-aminohexafluoro-6-iminocyclohex-1-enecarbonitrile was formed, again by stepwise addition-elimination.