O. A. Sadigov, H. M. Alimardanov, Sh. I. Ismailova
Jun 1, 2020
Citations
0
Influential Citations
0
Citations
Journal
Russian Journal of Organic Chemistry
Abstract
2-Aminocyclododecan-1-ol and 6(3)-aminodecahydro-1,4-ethanonaphthalen-5(2)-ols (mixture of isomers) were synthesized in two steps via oxidative hydroxybromination of cyclododecene and 1,2,3,4,4a,5,6,8a(1,4,4a,5,6,7,8,8a)-octahydro-1,4-ethanonaphthalines with the system hydrogen peroxide–HBr. In the first step, oxidation of hydrogen bromide with hydrogen peroxide generated intermediate dioxidanium bromide which added to the C=C double bond of the unsaturated substrate to give the corresponding α-bromo alcohols. In the second step, substitution of the bromine atom by amino group in the presence of an alkali afforded α-amino alcohols.