854899-02-8

Upstream product

• 13464-19-2 phenyl chlorothioformate 
• 106-47-8 4-chloro-aniline 
• 887235-26-9 S-4-pentynyl N-(4-chlorophenyl)-N-[(4-methylphenyl)sulfonyl]carbamothioate 
• 108-98-5 thiophenol 
• 2903-34-6 4-methyl-N-(4-chlorophenyl)benzenesulfonamide 
• 104-12-1 p-chlorphenylisocyanate 

Downstream Products

• 6333-41-1 N-butyl-N’-(4-chlorophenyl)urea 

Relevant academic research and scientific papers

Kinetics and mechanism of the anilinolysis of S-aryl N-arylthiocarbamates in acetonitrile

The aminolysis reactions of S-aryl N-arylthiocarbamates (YC 6H4NH-C(=O)-SC6H4Z, 1) with anilines in acetonitrile are studied. The reaction rates are more influenced by the nucleophilicity of the nucleophile than the nucleofugality of the leaving group, but the change In the effective charge from reactants to the TS for formation of the tetrahedral intermediate is slightly greater in the leaving group (βz from-0.07 to -0.14) than In the nucleophile (βx = 0.04-0.12). The magnitude of the Broensted coefficients are in the range of values that are consistent for a stepwise mechanism with rate-limiting formation of the zwitterionic tetrahedral intermediate. Signs of cross-interaction constants, ρxy (>0), ρxz (>0) and ρyz (0), are all consistent with a stepwise mechanism. It Is concluded that the change of the amine from benzylamines to anilines causes a shift of the aminolysis mechanism from a concerted to a stepwise process. Copyright

Generation and cyclization of unsaturated carbamoyl radicals derived from S-4-pentynyl carbamothioates under tin-free conditions

The radical reaction of benzenethiol with S-4-pentynyl carbamothioates provides a valuable protocol for the tin-free generation of carbamoyl radicals, which arise from intramolecular substitution at sulfur by the initial sulfanylvinyl radicals. This procedure can be usefully employed to achieve N-benzylcarbamoyl radical 5-exo and 4-exo cyclizations leading, respectively, to pyrrolidinones and azetidinones, although, for the latter, it seems of lesser utility. Novel evidence is presented that. N-tosyl-substituted carbamoyl radicals display a peculiar tendency to yield the corresponding isocyanate by β-elimination of the tosyl radical.