Hexanecarbonitrile

A 25-ml Schlenk tube was charged with the step 2 product mixture (1.76 or 2.00 g) dissolved in 2 or 9 ml of either THF or toluene. All samples were free radically initiated using either 2,2 -azobis(isobutyrylnitrile) (Vazo 64) or l,l -azobis(cyclo-hexanecarbonitrile) (Vazo 88). Each tube was then sealed with a rubber septum and then degassed by three cycles of freeze-thaw pumping and then heated to 60°C for selected times. After cooling to ambient temperature, the mixture was precipitated in 20 ml petroleum ether and then isolated and washed with cold petroleum ether and the product isolated. 

Malononitrile over potassium tetrafluorocobaltate(III) gives a mixture of at least 35 products and the benzonitrile product is almost as complex." However, over cesium tetra-fluorocobaltate(III) at 300°C, benzonitrile gives100 a much simpler mixture and perfluorocyclo-hexanecarbonitrile (ca. 30%) is the major product, with perfluorocyclohexane and per-fluorobenzonitrile as minor ones. Perfluorobenzonitrile is converted, in over 50% yield, by both cobalt(III) fluoride (165-170°C) and potassium tetrafluorocobaltate(III) (210°C), into mainly the nonconjugated monoene perfluoro(cyclohex-3-enecarbonitrile). 

Hydroxy-1 -cyclo-hexanecarbonitrile 2-Hydroxy-3,5-diiodobenzoic acid 2 -Hydroxy-4, 6 -di-methylaceto-phenone... 

MESITYLENESULFONYLHYDRAZINE, AND (1a,2a,6P)-2,5-DIMETHYLCYCLO-HEXANECARBONITRILE AND (1a,2P,6a)-2,6-DIMETHYLCYCLO-HE XAN ECARBONITRILE AS A RACEMIC MIXTURE... 

Mesitylenesulfonyl Hydrazine and (la,2a,6(3)-2,6-Dimethylcyclo-hexanecarbonitrile and (1a,2p,6a)-2,6-Dimethylcyclohexane-carbonitrile. 

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