Add time:08/13/2019         Source:sciencedirect.com

Kinetic study of the catalytic oxidation of cis- and trans-4-t-Bu-cyclohexanol by 2-cyclohexenone shows that the cis isomer is the more reactive. This result is attributed to the fact that the hydroxyl group in the axial position is more apt to form a bond with rhodium than is the equatorial one. In the absence of a hydrogen acceptor, RhH(PPh3)4 induces isomerisation of the hydroxyl group from the axial (or equatorial) to equatorial (or axial) position. The small amount of 4-t-Bu-cyclohexanone observed during the isomerisation is probably a reaction intermediate. This reaction shows that the isomerisation of α- or β-D-glucose, in aprotic solvent and with the same catalyst, does not necessarily involve a ring opening.

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