Some stereochemical relationships among sulfoxides, sulfilimines, and sulfoximines

✍ Scribed by Michael A. Sabol; Richard W. Davenport; Kenneth K. Andersen

• Book ID: 104222900
• Publisher: Elsevier Science
• Year: 1968
• Tongue: French
• Weight: 102 KB
• Volume: 9
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)89710-5

✦ Synopsis

Recently S,S-dimethyl-N-benzenesulfonylsulfoximine has been obtained by the reaction of dimethyl sulfoxide with benzenesulfonyl azide (2). We wish to report our findings concerning the stereochemical course of this reaction. When (R)-methyl p-tolyl sulfoxitie (I) (m.p. 74.5-75.5, [a], 25 + 155 (c. 1.6, acetone)) was reacted with p-toluenesulfonyl azide in the presence of copper, optically active S-methyl-~-p-tolyl-N-p-toluenesulfonylsulfoximine (IIa) (m.p. 158.5-159.5, [CC], 24 -130 (c. 1.6, acetone)) was obtained. The configuration