Critical micelle concentrations were determined for 2-octylammonium and 2-octyltrimethylammonium ions in the presence of various counterions. The kinetics and the stereochemistry of the aqueous nitrous acid deamination of 2-aminooctane were studied under micellar and nonmicellar conditions. Micellar catalysis of the deaminative rate (about 15-fold) was observed. Some catalysis was observed, whatever the identity of the anions present during the deamination. The stereochemistry of the 2-aminooctane to 2-octanol conversion could be changed from 24 % net inversion (nonmicellar) to 6% net retention, under certain micellar deamination conditions. In contrast to the kinetic results, the stereochemical effects were highly dependent on the identity of the counterions.

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Optically active octane 2-diazotate (160) was hydrolyzed with H2180. Product 2-octanol was converted to the l-acetyl lactate diastereomers, which were separated by glpc and analyzed for l80 content by mass spectroscopy. From the (glpc) stereochemical data and the lsO analyses, 2-octanol formation could be partitioned into four pathways: 160 conservation-retention, 160 conservation-inversion, 160 exchange-retention, and lsO exchange-inversion. The percentages corresponding to the above pathways, for the H2180 hydrolysis of dry octane 2-diazotate (leO) were 26.6, 16.7, 13.8, and 43.1%, respectively. The results are discussed in terms of an intermediate cationic 2-octyl moiety which largely fails to become symmetrically hydrated before collapse to 2-octanol. Consequences for the study of deamination reactions are highlighted.