7429-01-8

Upstream product

• 98-91-9 thiobenzoic acid 
• 98-83-9 isopropenylbenzene 
• 201611-77-0 cumyl dithiobenzoate 
• 98-88-4 benzoyl chloride 

Relevant academic research and scientific papers

Radical-induced oxidation of RAFT agentsa - A kinetic study

Radical-induced oxidation of reversible addition-fragmentation chain transfer (RAFT) agents is investigated with respect to the effect of molecular structure on oxidation rate. The radicals are generated by homolysis of either azobisisobutyronitrile or alkoxyamine and transformed in situ immediately into peroxy radicals through transfer to molecular oxygen. It is found that the oxidation rate depends on the structure of Z- and R-group of thiocarbonylthio compounds. For dithioesters with identical Z-phenyl substituent, the oxidation rate decreases in the order of cyanoisopropyl (-C(Me)2CN) > cumyl (-C(Me)2Ph) > phenylethyl (-CH(Me)Ph) > 2-methoxy-1-methyl-2- oxoethyl (-CH(Me) -C(=O)OCH3) > benzyl (-CH2Ph). For dithioesters with identical R-group, the oxidation rate decreases in the order of Z = phenyl- ～ benzyl- > RS- (trithiocarbonates) > RO- (xanthates). The stability of the RAFT agents toward oxidation correlates well with the chain transfer abilities as those previously reported by Rizzardo and coworkers. The priority of the oxidation reaction over the RAFT process, and the subsequent influence on RAFT polymerization are also investigated.

Montmorillonite K 10-catalyzed regioselective addition of thiols and thiobenzoic acids onto olefins: An efficient synthesis of dithiocarboxylic esters

The addition of thiols and thiobenzoic acids onto olefins proceeded regioselectively in a Markovnikov manner in the presence of Montmorillonite K 10 (Mont K 10) clay as the catalyst to afford thioethers and thiocarboxylic S-esters, while high selectivity to anti-Markovnikov products was realized in the absence of any catalyst. Treatment of the esters with Lawesson's reagent provided the corresponding dithiocarboxylic esters in high yields.