Investigation into the Regiochemistry of 1,3-Dipolar Cycloaddition of C,N-Diphenyl Nitrone with Some Vinyl Sulfoximines as Dipolarophile: Theoretical Studies

✍ Scribed by Farid Moeinpour

• Publisher: John Wiley and Sons
• Year: 2011
• Tongue: English
• Weight: 144 KB
• Volume: 29
• Category: Article
• ISSN: 0256-7660
• DOI: 10.1002/cjoc.201180262

✦ Synopsis

Abstract

The regiochemistry of 1,3‐dipolar cycloaddition reactions of C,N‐diphenyl nitrone with some vinyl sulfox‐ imines as dipolarophile was investigated using density functional theory (DFT)‐based reactivity indexes and activation energy calculations at B3LYP/6‐31G(d) level of theory. Analysis of the geometries and bond orders (BOs) at the TS structures associated with the different reaction pathways shows that these 1,3‐dipolar cycloaddition reactions occur via an asynchronous concerted mechanism. Analysis of the local electrophilicity and nucleophilicity indexes permits an interpretation about the regioselectivity of these 1,3‐dipolar cycloaddition reactions. The theoretical results obtained in the work clearly predict the regiochemistry of the isolated cycloadducts and agree to experimental outcomes.