Preparation of 3-Oxocyclohex-1-ene-1-carbonitrile

Abstract

Chromium trioxide oxidation of cyclohexenecarbonitrile efficiently provides analytically pure 3-oxocyclohex-1-ene-1-carbonitrile. The procedure is described in detail, providing a very reliable, one-step synthesis of a highly versatile oxonitrile.

Key words

oxonitrile - nitrile - oxidation - synthesis

References

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• 18b

  The lack of oxidation may be due to competitive metal ligation of the nitrile as occurs with dirhodium(II) caprolactamate: Doyle M. P. personal communication.

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Assaying several different solvent mixtures identified CH₂Cl₂-hexanes (1.5:1) as optimal, although a stepped EtOAc-hexanes gradient (3:17, 1:4, 1:3) permitted isolation of 2.30 g of 2 in 64% yield.