Tetrahedron

Thallium in organic synthesis—XVI: Preparation of p-quinones by oxidation of phenols and hydroquinones with thallium (III) trifluoroacetate

A McKillop, BP Swann, EC Taylor

Index: McKillop,A. et al. Tetrahedron, 1970 , vol. 26, p. 4031 - 4039

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Citation Number: 80

Abstract

Treatment of 2, 6-disubstituted-4-t-butylphenols with thallium (III) trifluoroacetate in either trifluoroacetic acid or carbon tetrachloride as solvent results in loss of the 4-t-butyl substituent as isobutene and formation in high yield of the corresponding 2, 6-disubstituted p- quinones. Possible mechanisms for this novel reaction, which probably proceeds via the intermediacy of a hydroquinone or hydroquinone mono-trifluoroacetate ester, are ...