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New reactions of thiobenzophenone s-methylide

✍ Scribed by Li Xingya; Rolf Huisgen

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
229 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

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 -78'C in THF to furnish quantitatively 2,2diphenyl-1 ,3,4-thiadiazoline (g, which eliminates nitrogen at -45'C with a half-life of 55 min. 1 The intermediate th iobenzophenone S-methyl ide (2) undergoes head-head dimerization to give the 1 ,4dithiane derivative 2. iC&l,C=S

πŸ“œ SIMILAR VOLUMES

Reactions of Thiobenzophenone S-Methylid
Reactions of Thiobenzophenone S-Methylide with Thiocarbonyl Compounds
✍ Rolf Huisgen; Xingya Li; Grzegorz Mloston; Claudia Fulka πŸ“‚ Article πŸ“… 2000 πŸ› John Wiley and Sons 🌐 English βš– 352 KB πŸ‘ 1 views

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

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