spectrum of I had a quartet at 4.62,12 a singlet at 8.51, and a doublet at 8.60, which partially overlapped the singlet. These absorptions are assigned to the methine, gem-dimethyl, and methyl protons, respectively, of 2methylbutene-2 ozonide. The methyl:methine peak area ratio was 9.4:1. The spectrum of II has a triplet at 5.13, a multiplet at 8.56, a singlet at 8.83, and a triplet at 9.30. These are assigned to the methine, methylene, gem-dimethyl, and methyl protons, respectively, of 2-methylpentene-2 ozonide. The integrated areas were 1:8:3.16 for methine:gem-dimethyl plus methylene: methyl. Yields of the ozonides were 2.09, 2.22, 4.92, 2.0, and 2.06 mmoles, respectively, for the ozonides of butene-2, 2-methylbutene-2, pentene-2, 2-methylpentene-2, and hexene-3 (total yield of ozonides = 21.6%).We are presently investigating the possibility of obtaining ozonides from the remaining unobserved zwitterion-carbonyl combination, that is, the reaction of ketonic zwitterions with simple ketones.Acknowledgment. L. D. L. wishes to thank the Director of the Rubber and Plastics Research Association of Great Britain for a 1 year leave of absence, during which time this work was carried out.(12) All n.m.r. results are reported as -values with tetramethylsilane as external standard.
