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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Die Stereochemie der Desaminierung der primären Amine (I) durch salpetrige Säure wird in Gegenwart zahlreicher Zusatzmittel, z.B. Natrium‐ oder Tetraalkylammoniumbromiden, untersucht.