(1S,2R,2'S)- and (1S,2S, 2'S)-1-phenyl-2-phenylthio-2-(tetrahydropyran-2'-ylthio)ethanol diastereoisomers at 193 K.
In the synthesis of 1-phenyl-2-phenylthio-2-(tetrahydropyran-2-ylthio)ethanol, C(19)H(22)O(2)S(2), four diastereoisomers are formed. Two non-centrosymmetric enantiomeric forms which crystallize in space groups P2(1)2(1)2(1) and Pna2(1) are presented. The former has an intramolecular hydrogen bond between the hydroxyl group and the O atom of the tetrahydropyran ring. In the latter isomer, the hydroxyl group forms an intermolecular hydrogen bond to the O atom of the tetrahydropyranyl group of a neighbouring molecule, joining the molecules into chains in the c-axis direction; the O.O distances are 2.962 (4) and 2.764 (3) A, respectively. The tetrahydropyran rings are in chair conformations in both isomers and the S side chain has an equatorial orientation in the former, but an axial orientation in the latter molecule.
Kansikas
J
J
Department of Chemistry, Laboratory of Inorganic Chemistry, PO Box 55, 00014 University of Helsinki, Finland. jarno.kansikas@helsinki.fi
Sipilä
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