91875-38-6Relevant academic research and scientific papers
Synthesis of new β,β'-diketodithioethers via swern oxidation and study of their hydrazone formation rate
Seyedi, Seyed Mohammad,Sadeghian, Hamid,Safari, Zohreh
experimental part, p. 2297 - 2306 (2010/03/31)
The synthesis of β,β'-diketodithioethers 4b-j from corresponding β,β'-dihydroxydithioethers 3b-j was carried out by a Swern oxidation using DMSO-oxalyl chloride as oxidizing agent. β,β'- Dihydroxydithioethers 3b-j were prepared by the reaction of two molar equivalents of epoxides 1b-j with dimercaptoethane 2 in the presence of a saturated aqueous solution of potassium carbonate. The reactivity behavior of imine formation of the β,β'-diketodithioethers 4b-j by 2,4-dinitrophenylhydrazine was also investigated, and a mechanism was proposed by using molecular orbital (MO) calculations. To confirm the proposed mechanism, the role of the thia function to activate hydrazone formation by measuring HOMO-LUMO energy levels was also demonstrated.
