7-Phenyl-1-oxa-4-thiaspiro[4.5]decan-7-ol stereoisomers

Abstract

The stereoisomers of 7-phenyl-1-oxa-4-thiaspiro[4.5]decan-7-ol, C(14)H(18)O(2)S, have the same stereochemistry at the C atom bearing an OH group, i.e. axial OH and equatorial phenyl groups. However, the acetal S and O atoms are axial and equatorial, respectively, in one isomer and reversed in the second. Furthermore, the crystals of one isomer are composed of hydrogen-bonded molecules involving the hydroxyl H atom and the O atom of the five-membered heterocyclic ring, with an O.O distance of 2.962 (3) A, forming a polymeric chain along the b axis. The asymmetric unit of the other isomer is composed of two molecules, wherein hydroxyl H atoms and the O atoms of the five-membered heterocyclic rings display intramolecular O-H.O hydrogen bonds with O.O separations of 2.820 (2) and 2.834 (2) A.

On the Reaction of 1-Oxa-4-thiaspiro[4.5]decan-7-one with PhLi. A Reinvestigation

“…The stereochemical characterization from spectral features alone was difficult and, hence, single-crystal X-ray analyses were performed. 5 The alcohols were indeed 2a and 2b as expected from the ground-state conformational distribution of 1 into 1a and 1b. The ORTEP plots of 2a and 2b are given in the Supporting Information (Figures 1 and 2).…”

“…The alcohols were separated by radial chromatography and characterized. The stereochemical characterization from spectral features alone was difficult and, hence, single-crystal X-ray analyses were performed . The alcohols were indeed 2a and 2b as expected from the ground-state conformational distribution of 1 into 1a and 1b .…”