Stereochemistry of Nitrogen Heterocycles. Transformations of Stereoisomeric 1-chloro-2-methyl-4-keto-trans-decahydroquinolines in an acidic medium

Autor: Litvinenko, G. S., Voronenko, L. A., Isakova, L. A.
Zdroj: Chemistry of Heterocyclic Compounds; August 1988, Vol. 24 Issue: 8 p906-914, 9p
Abstrakt: It is shown that epimeric [with respect to the C(2) atom] 1-chloro-2-methyl-4-keto-trans-decahydroquinolines in an acidic medium undergo intermolecular monochlorination in the a position relatve to the carbonyl group with the formation of epimeric [with respect to the C(2) atom] 3e-chloro- and 10a-chloro-2-methyl-4-keto-trans-decahydroquinolines and 2-methyl-4-keto-10-chloro-cis-decahydroquinolines. The mechanism of the transformations is examined, and an assumption regarding the possibility of cis-trans isomerization of the intermediately formed p-chloronium complex is expressed.
Databáze: Supplemental Index