Title : ( Synthesis of New β,β -Diketodithioethers via Swern Oxidation and Study of Their Hydrazone Formation Rate )
Authors: Seyed Mohammad Seyedi , Hamid Sadeghian , ,
Full TextAbstract
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.
Keywords
, Ab initio; 2, 4-dinitrophenylhydrazine; HUMO-LUMO; molecular orbital calculation; neighboring group participation
@article{paperid:1013652,
author = {Seyedi, Seyed Mohammad and Sadeghian, Hamid and , },
title = {Synthesis of New β,β -Diketodithioethers via Swern Oxidation and Study of Their Hydrazone Formation Rate},
journal = {Phosphorus, Sulfur, and Silicon and the Related Elements},
year = {2009},
volume = {184},
number = {9},
month = {September},
issn = {1042-6507},
pages = {2297--2306},
numpages = {9},
keywords = {Ab initio; 2;4-dinitrophenylhydrazine; HUMO-LUMO; molecular orbital calculation; neighboring group participation},
}
%0 Journal Article
%T Synthesis of New β,β -Diketodithioethers via Swern Oxidation and Study of Their Hydrazone Formation Rate
%A Seyedi, Seyed Mohammad
%A Sadeghian, Hamid
%A ,
%J Phosphorus, Sulfur, and Silicon and the Related Elements
%@ 1042-6507
%D 2009
