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A review of the literature concerning reactions of ozone with amines has given rise to the working hypothesis that these reactions all involve initially the electrophilic attack of ozone to give an adduct for which at least three different reaction routes are available: loss of molecular oxygen to give an amine oxide or further reaction products thereof, an intramolecular oxidation of a side chain, and dissociation to nitrogen cation radicals and the ozonate anion radical, followed by further reactions of these. Results from ozonations of tert-butylamine and tri-n-butylamine, which furnish additional evidence for the above competitions, are described.>Tphe literature suggests several ways in which ozone reacts with amines.

The solution was refluxed for 24 hr. and the sulfide was isolated in the manner described for XVIII; 76 mg. (22%) of light yellow oil which was about 95% pure (by gas-liquid chromatography) was obtained. Microfractionation yielded a colorless liquid.Anal. Caled, for C,2H24S: C, 71.95; H, 12.08. Found: C, 72.08; H, 12.12. Thiacycloundecane (XXlI).-The above procedure duplicated with 11.5 g. (0.038 mole) of 1,10-dibromodecane (XX) (Fisher Scientific Corp.) yielded 850 mg. (13%) of 96+% pure (g.l.c.) thiacycloundecane, b.p. 66-68°( 0.2 mm.).

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