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Reactions of Thiobenzophenone S-Methylide with Thiocarbonyl Compounds

✍ Scribed by Rolf Huisgen; Xingya Li; Grzegorz Mloston; Claudia Fulka

Publisher
John Wiley and Sons
Year
2000
Tongue
English
Weight
352 KB
Volume
2000
Category
Article
ISSN
1434-193X

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✦ Synopsis

2,5-Dihydro-2,2-diphenyl-1,3,4-thiadiazole (4) eliminates N 2 at -45 Β°C and generates thiobenzophenone S-methylide (5), which is intercepted by dipolarophiles. The 1,3-cycloadditions of 5 with thiones (aromatic and aliphatic thioketones, dithioesters, trithiocarbonate) furnish 1,3-dithiolanes 7, in which the substituents, even voluminous ones, appear in the proximal 4-and 5-positions. The reaction of 5 with adamant-

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New reactions of thiobenzophenone s-meth
New reactions of thiobenzophenone s-methylide
✍ Li Xingya; Rolf Huisgen πŸ“‚ Article πŸ“… 1983 πŸ› Elsevier Science 🌐 French βš– 229 KB

prepared from thiobenzophenone and diazomethane at -78'C, extrudes N2 at -45'C and allows to study in situ 1,3-cycloadditions of thiobenzophenone S-methylide (3\_) with electrophilic C=S, C=C, C%, and N=N bonds. We reported recently that thiobenzophenone combines with one equiv. of diazomethane at -

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 πŸ“‚ Article πŸ“… 2005 πŸ› John Wiley and Sons 🌐 English βš– 259 KB πŸ‘ 1 views

## 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