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Conformational studies of 2-anilino-substituted 1,3,2-oxazaphospholanes

✍ Scribed by William N. Setzer; Mark N. Flair; Xiao-Jing Yang; Chia-Kuei Wu; Edward J. Meehan

Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
828 KB
Volume
5
Category
Article
ISSN
1042-7163

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✦ Synopsis

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.

📜 SIMILAR VOLUMES

Solid-state conformation of the 1,3,2-ox
Solid-state conformation of the 1,3,2-oxazaphospholane ring in 2-dialkylamino-3,4-dimethyl-5-phenyl-1,3,2-oxazaphospholane sulfides
✍ Rafal Kruszynski; Tadeusz J. Bartczak; Piotr Majewski 📂 Article 📅 2001 🏛 John Wiley and Sons 🌐 English ⚖ 107 KB

## Abstract Dialkylamino‐3,4‐dimethyl‐5‐phenyl‐1,3,2‐oxazaphospholane sulfides (where the alkyl is an isopropyl, ethyl or methyl group) was obtained by sulfurization of the respective phospholanes. The structures of these compounds were determined by X‐ray crystal structure analysis. Five‐membered