STEREOCHEMISTRY OF NITROGEN HETEROCYCLES. 67. TRANSFORMATIONS OF STEREOISOMERIC 1-CHLORO-2-METHYL-4-KETO-trans-DECAHYDROQUINOLINES IN AN ACIDIC MEDIUM

Article abstract of DOI:10.1007/BF00479348

It is shown that epimeric 1-chloro-2-methyl-4-keto-trans-decahydroquinolines in an acidic medium undergo intermolecular monochlorination in the α position relative to the carbonyl group with the formation of epimeric 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 ?-chloronium complex is expressed.