Abstract

The products of epoxidation of norbornene, cyclohexene, and adamantylideneadamantane with pentafluoroiodobenzene using as catalysts variously substituted tetraphenylporphyrin complexes of chloroiron (III), chloromanganese(III), and chlorochromium(III) have been determined. All catalysts afforded the epoxide from adamantylideneadamantane, suggesting that the metallacycle intermediate, impossible in this case, is not required for epoxidation. The electronegatively substituted iron porphyrins show a great tendency toward epoxidation rather than allylic oxidation and show more selectivity for cis-alkenes.

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