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Cover Picture: Cycloadditions and Methylene Transfer in Reactions of Substituted Thiocarbonyl S-Methylides with Thiobenzophenone: A Computational Study (Eur. J. Org. Chem. 8/2005)

✍ Scribed by Reiner Sustmann; Willi Sicking; Rolf Huisgen

Publisher: John Wiley and Sons
Year: 2005
Tongue: English
Weight: 57 KB
Volume: 2005
Category: Article
ISSN: 1434-193X
DOI: 10.1002/ejoc.200590016

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✦ Synopsis

Abstract

The cover picture shows the potential energy diagram of methylene transfer from 4,4,5,5‐tetramethylcyclopentanethione S‐methylide to thiobenzophenone via a biradical intermediate which wins over a possible formation of regioisomeric cycloadducts. Methylene transfer reactions together with 1,3‐dipolar cycloadditions of other thiocarbonyl S‐methylides to thiones are described by R. Huisgen et al. on p. 1519 ff. DFT calculations on the mechanism of these reactions, concerted or stepwise, are reported by R. Sustmann et al. on p. 1505 ff.

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Cycloadditions and Methylene Transfer in

Cycloadditions and Methylene Transfer in Reactions of Substituted Thiocarbonyl S-Methylides with Thiobenzophenone: A Computational Study

✍ Reiner Sustmann; Willi Sicking; Rolf Huisgen 📂 Article 📅 2005 🏛 John Wiley and Sons 🌐 English ⚖ 259 KB

## Abstract Regiochemistry and methylene transfer reactions in cycloadditions of aliphatic thiocarbonyl __S__‐methylides and thiobenzophenone are analyzed by ab initio [(U)HF/3‐21G\*] and DFT calculations [(U)B3LYP/6‐31G\*//(U)HF/3‐21G\* and (U)B3LYP/6‐31G\*]. The formation of regioisomeric 1,3‐dit