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Ozonolyses of 0-methyloximes (4) of 5, 6and ?'-membered cycloketones in the presence of esters of trifluoroacetic acid (5) or of acyl cyanides (6) afforded ozonides of types 7 and 8 , respectively, which are formally derived from vinyl ethers or vinyl cyanides. Similarly, ozonolysis of the 0-methylated oxime of acetone (9) in the presence of esters of trifluoroacetic acid (5) and of the 0-methylated oxime of 2-naphthaldehyde (11) in the presence of acyl cyanides (6) gave the corresponding ozonides of types 10 and 12, respectively.Ozonolysis reactions of compounds having C = N bonds have been reported repeatedly [']. They proceeded at slower rates than those of compounds containing C=C bonds, and in most cases no peroxidic products were obtained. By contrast, ozonolysis of 1 was reported to give a mixture of the stereoisomers of 2 in a yield of 22%E21. This could be rationalized by cleavage of 1 by ozone to give carbonyl oxide 3, followed by a [3 + 31 cycloaddition of 3 to give 2.

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