Ring Transformations of 3-Phenyl-4-Tosylimino-1, 3-Thiazetidine-2-One

✍ Scribed by Gerrit L'abbé; Jean-Paul Dekerk; Martine Deketele

• Publisher: Wiley (John Wiley & Sons)
• Year: 2010
• Weight: 252 KB
• Volume: 91
• Category: Article
• ISSN: 0037-9646
• DOI: 10.1002/bscb.19820910310

✦ Synopsis

Abstract

The title compound 1 can be transformed into functionalized 5‐ and 6‐ membered heterocycles by treatment with nucleophilic reagents. For instance, the reaction of 1 with tert‐butyl isonitrile yields the two isomers 2 and 3, resulting from different positions of attack at the 4‐membered ring. Diethylaminopropyne, on the contrary, reacts only at the C~2~‐position of 1 giving rise to the 6‐membered ring 4 in high yield. With phosphorus ylides, three pathways, all resulting from initial attack at the C~2~‐atom of 1, have been observed depending on the substitution pattern of the ylide.