Configurational assignments in some dihydrobenzo[c]thiophenes by NMR solvent effects. Correlation of the relative chemical shifts of α-methyl groups with sulphoxide stereochemistry

✍ Scribed by Ishai Sataty

• Publisher: John Wiley and Sons
• Year: 1974
• Tongue: English
• Weight: 387 KB
• Volume: 6
• Category: Article
• ISSN: 0749-1581
• DOI: 10.1002/mrc.1270060104

✦ Synopsis

Abstract

The configuration of isomeric 3,3‐dimethyl‐1‐phenyl‐1,3‐dihydrobenzo[c]thiophene 2‐oxides was assigned on the basis of selective benzene‐ and TFA‐induced NMR shifts. The same method was employed for assigning the α‐methyl resonances of these sulphoxides. Examination of NMR data for a variety of cyclic sulphoxides revealed that in CCl~4~ or CDCl~3~ solution, α‐hydrogen cis to SO often resonates at higher magnetic field, while α‐methyl group cis to SO characteristically resonates at lower field, than the same hydrogen or methyl group trans to SO, respectively.