Journal of the Chemical Society. Perkin transactions I p. 871 - 874 (1996)
Update date:2022-08-30
Topics:
Kuwabara, Hajime
Ushigoe, Yoshihiro
Nojima, Masatomo
Carbonyl oxides, derived from the ozonolyses of vinyl ethers, readily undergo [3 + 2] cycloadditions with acyl cyanides affording the corresponding cyano-substituted 1,2,4-trioxolanes in isolated yields of 34-88%. In competition experiments, a relative order of reactivity of the carbonyl oxide trapping agents was tentatively deduced; trifluoroacetophenone > α,α-diphenyl-N-methylnitrone (N-methyldiphenyl-methylideneamine N-oxide) > benzoyl cyanide > methyl benzoylformate > α,α,N-triphenylimine [N-(diphenylmethylidene)aniline] ? benzaldehyde. As expected from the electron-withdrawing ability of the cyano group, 3-cyano-3-phenyl-1,2,4-trioxolane oxidized not only triphenylphosphine but also methyl p-tolyl sulfide and 2,3-dimethylbut-2-ene very easily.
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