Rearrangement of epoxy-ethers providing carbonyl compounds was catalyzed by tetracyanoethylene (TCNE) in acetonitrile under the preferential anchimetric assistance of intramolecular etheric oxygen function in the 5-exo mode for the 1,2-disubstituted epoxide unit and in the quaternary 5-exo, 5-endo, and 6-endo mode for the trisubstituted type. In acetone, epoxy-ethers favored by neighboring group participation were led to carbonyl compounds and the other epoxides furnished acetonides.
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Masaki et al. (1993) studied this question.
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