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Conformational analysis of 7-membered dimethyl cyclic sulphites: 2-Oxo-1,3,2-dioxathiepanes and 3-oxo-2,4,3-dioxathiepins

✍ Scribed by Afonso Celso Guimaraes; Paulo Gontijo Veloso de Almeida; Michel Baltas; Louis Cazaux

Publisher
John Wiley and Sons
Year
1983
Tongue
English
Weight
606 KB
Volume
21
Category
Article
ISSN
0749-1581

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✦ Synopsis

Abstract

2‐Oxo‐1,3,2‐dioxathiepanes and 3‐oxo‐2,4,3‐dioxathiepins, including two series of three diastereoisomers, were synthesized, isolated by HPLC and characterized by ^1^H and ^13^C NMR spectroscopy. Their conformational behaviour was studied using a computer‐assisted LIS technique and, for c‐4, t‐7‐dimethyl‐2‐oxo‐1,3,2‐dioxathiepane, a 400 MHz spectral analysis. Single twist‐chair conformations or an equilibrium between them are the most stable in the dioxathiepane series while chair or twist‐boat forms, or both in equilibrium, are favoured in the dioxathiepin series. Conformations and equilibria are detailed, with and without LSR, taking into account ^1^H coupling constants and IR SO stretching frequencies as conformational probes.

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