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. 1994 Mar 15:50 ( Pt 3):425-8.
doi: 10.1107/s0108270193009321.

(4aR,8R,SR)-8-(p-tolylsulfinyl)-2,3,4,4a,5,6,7,8-octahydro-4a-quinolinol

P D Robinson  1 , D H Hua, H Wang, J S Chen, L A Good
Affiliations

(4aR,8R,SR)-8-(p-tolylsulfinyl)-2,3,4,4a,5,6,7,8-octahydro-4a-quinolinol

P D Robinson et al. Acta Crystallogr C. .

Abstract

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.

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