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A detailed study of the ozonation of two primary amines, w-butylamine (having a primary alkyl group) and isopropylamine (having a secondary alkyl group), has been made and the results have been compared with those of ferf-butylamine in regard to the three principal fates of the initial amine-ozone adduct.

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36mined in a like manner with A = 4 mm and B = 4 mm. Other diffractometer parameters and the method of estimation of standard deviations have been described previously.10 As a check on the stability of the instrument and the crystal, two reflections, the (200) and (002), were measured after every 30 reflections; no significant variation was noted.One independent quadrant of data was measured out to 28 = 1 10"; a total of 349 unique reflections ( I > 2 4 ) ) was obtained.The intensities were corrected for Lorentz and polarization effects but not for absorption, since the extreme values of the transmission factors were 0.90 and 0.95. The full-matrix. least-squares refinement was carried out using the Busing and Levy program O R F L S .~~ The function w(lF,l -I F c ( ) l 3 was minimized. No corrections were made for extinction or anomalous dispersion. Neutral atom scattering factors were taken from the compilations of Cromer and Waberl4 for C and N: those for hydrogen were from "International Tables for X-ray Crystallography." Final bond distances. angles, and errors were computed with the aid of the Busing, Martin, and Levy ORFFE program.16 Crystal structure illustrations were obtained with the program ORTEP.~' Fourier calculations were made with the A L F F~~ program. ~ ~~ Abstract:The formation and characterization of the first x complexes observed between ozone and aromatic or olefinic x systems are described. A correlation was made between the ionization potentials of a group of aromatic substrates and the wavelength of the absorption of their ozone complexes in the visible region. Two of the complexes were allowed to react with certain cis and trans olefins. The cis-trans ratios of the ozonides produced were different from those of the ozonides obtained by ozone alone in the cases of the cis-and rrans-l,2-diisopropylethylenes. However, there was no appreciable difference in the results obtained using complexed or uncomplexed ozone with the less bulky cis-and trans-3-hexenes.

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