Stereochemistry of the conventional and modified Bucherer–Bergs reactions of 2-substituted cyclohexanones Journal Articles uri icon

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abstract

  • The configurations of the spiro-hydantoins produced from 2-methyl- and 2-phenylcyclohexanone, 2,6-dimethylcyclohexanone, and dl-menthone by either the conventional Bucherer–Bergs (B•–B•) reaction, or a variant employing COS or CS2 in place of CO2, have been established by 13C nmr. In all cases the conventional B•–B• reaction gave the hydantoin having the 4′-carbonyl group equatorial, and the COS or CS2 variant, the mono- or dithiohydantoin having the 4′-thiocarbonyl group, axial.

publication date

  • August 1, 1982