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- Publisher
- Wiley
- Copyright
- Copyright © 1994 Wiley Subscription Services
- ISSN
- 1042-7163
- eISSN
- 1098-1071
- DOI
- 10.1002/hc.520050407
- Publisher site
- See Article on Publisher Site
Abstract
A series of 2‐anilino‐2‐thio‐1,3,2‐oxazaphospholanes derived from ephedrine has been synthesized and conformationally studied by proton NMR and X‐ray crystallography. The NMR data can be interpreted in terms of twist‐envelope conformations in which the anilino substituents on phosphorus adopt predominantly equatorial positions. X‐ray crystal structures of (2R,4S,5S)‐2‐anilino‐2‐thio‐3,4‐dimethyl‐5‐phenyl‐1,3‐2‐oxazaphospholane, (2R,4S,5S)‐2‐(4‐fluoroanilino)‐2‐thio‐3,4‐dimethyl‐5‐phenyl‐1,3,2‐oxazaphospholane, and (2R,4S,5S)‐2‐(4‐methoxyanilino)‐2‐thio‐3,4‐dimethyl‐5‐phenyl‐1,3,2‐oxazaphosholane have been carried out, and these compounds adopt envelop, twist‐envelope, and twist‐envelope conformations, respectively, with the anilino moieties equatorial.
Journal
Heteroatom Chemistry – Wiley
Published: Jan 1, 1994