Cyclohexane → Cyclohexanol

Participants

Reaction Conditions

Reaction Steps

A solution containing 1M cyclohexane, 0.625M 2,6-dichloropyridine N-oxide and 0.10 mM [Ru(TPFPP)(NO)(H2O)](SbF6) in 1 ml d6 -benzene was heated for eight hours in a sealed tube at 75° C. affording high yields of oxidized products. A combined yield of 93% and 1500 catalytic turnovers were obtained of two products, cyclohexanone and cyclohexanol (mole ratio 4:1). In CD2Cl2 the same reaction conditions proceeded to give 5600 turnovers to generate cyclohexanone and cyclohexanol (8:1) in a combined 98% yield in twelve hours. 2,6-dichloropyridine-N-oxide was unable to hydroxylate cyclohexane by heat alone as shown by a control experiment, proving that the ruthenium complex must be present to effect reaction. ##STR8##

Provenance & Evidence