(4aR,8R,SR)-8-(p-tolylsulfinyl)-2,3,4,4a,5,6,7,8-octahydro-4a-quinolinol.
The title compound, C16H21NO2S, isolated from the reaction of lithiated racemic 2,3,4,4a,5,6,7,8-octahydroquinoline with 0.5 equivalents of (-)-(1R,2S,5R)-menthyl (SS)-p-toluenesulfinate, possesses the unusual conformation in which the OH and bulky p-toluenesulfinyl groups are in axial positions. The S=O bond distance of 1.519 (3) A is longer than expected because of intramolecular hydrogen bonding between the hydroxyl group and the sulfinyl O atom.
Robinson
P D
PD
Department of Geology, Southern Illinois University, Carbondale 62901.
Hua
D H
DH
Wang
H
H
Chen
J S
JS
Good
L A
LA
D018360:Crystallography, X-Ray; D006860:Hydrogen Bonding; D006912:Hydroxyquinolines / Q000737:chemistry*; D008958:Models, Molecular; D013237:Stereoisomerism; D014105:Tosyl Compounds / Q000737:chemistry*
D006912:Hydroxyquinolines; D014105:Tosyl Compounds; C088183:8-(4-tolylsulfinyl)-2,3,4,4a,5,6,7,8-octahydro-4a-quinolinol