Oxidation of organic sulfides by N-halamine compounds

Date

2007-07-01

Author

Akdağ, Akın
Worley, S. D.

Metadata

Show full item record

This work is licensed under a Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License.

Item Usage Stats

173
views

0
downloads

N-halamine chemistry has been an important research topic in these laboratories for over two decades, offering many exciting opportunities both from practical and pedagogical points of view. One of these opportunities is in the use of polymer- and silica gel-bound N-halamines as selective oxidizing agents for organosulfur compounds. In this study, they have been employed to selectively oxidize organic sulfides including dimethyl sulfide and chloroethyl ethyl sulfide, the chemical mustard stimulant. The latter oxidation produced the less toxic sulfoxide derivative with about 70% conversion, with no sulfone produced, and only about 30% accompanying conversion to sulfoxide hydrolysis products. In this article, we report a combination of experimental and computational results.

Subject Keywords

Inorganic Chemistry, Organic Chemistry, Biochemistry

URI

https://hdl.handle.net/11511/56291

Journal

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS

DOI

https://doi.org/10.1080/10426500701247102

Collections

Department of Chemistry, Article

Suggestions

OpenMETU
Core

Synthesis of heteroaryl substituted dihydrofuran and dihydropyran derivatives by green chemistry approach Demirci, Sema; Tanyeli, Cihangir; Department of Chemistry (2009) The thesis subject is mainly involved in Green Chemistry approach. Thiophene, furan and pyridine carboxaldehydes were chosen as starting compounds and vinylation and allylation with Grignard reaction afforded the corresponding racemic heteroaryl substituted allylic and homoallylic alcohols. Subsequent resolution with enzymes (PS-Amano II, Lipozym and Novazym 435) gave enantiomerically enriched alcohols with the e.e. values varied between 65 and 99%. The absolute configurations of all substrates are known. A...
Synthesis of ferrocenyl cycloheptadienones Açıkgöz, Canet; Zora, Metin; Department of Chemistry (2005) Synthesis of seven-membered ring systems such as cycloheptadienones has attracted a great deal of attention in organic chemistry since they are present in a variety of biologically important molecules. Incorporation of the essential structures of such compounds with a ferrocene moiety instead of an aryl group could provide subtances with enhanced antitumor activities since some ferrocene derivatives have already proved to be active against a number of tumors. To develop a ferrocenyl-substituted seven-member...
Development of acyl anion precursors and their applications Reis, Ömer; Demir, Ayhan Sıtkı; Department of Chemistry (2005) This thesis presents the development of new acyl anion precursors and their applications. The main concern of this thesis was to make use of acyl anion precursors in catalytic bond forming reactions. Toward this aim, previously known cyanide ion catalyzed cleavage of benzils was investigated in scope and efficiency in unsymmetrical benzoin condensation. Although benzils were proved to be useful entities as acyl anion precursors in benzoin condensation, they suffer some major drawbacks. Therefore acylphospho...
Synthesis of beta-chloro-alpha-aminophosphonate derivatives via the regioselective ring opening of unactivated aziridine-2-phosphonates Polat-Cakir, Sidika; BEKSULTANOVA, Nurzhan; Doğan, Özdemir (Informa UK Limited, 2018-12-02) A series of unactivated racemic and chiral aziridine-2-phosphonates were synthesized by modified Gabriel-Cromwell reaction. Ring opening reaction of the synthesized phosphonates by gaseous HCl provided access to a wide range of biologically interesting novel beta-chloro-alpha-aminophosphonates. All reactions toward each of the above-mentioned products can be conducted regioselectively in high yields.
Synthesis and reactions of alpha-keto-beta-hydroxyphosphonates Barış, Şehriban; Demir, Ayhan Sıtkı; Department of Chemistry (2007) This thesis presents synthesis and different reactions of alpha-keto-beta-hydroxyphosphonates. Toward this aim, the hydroxyl functionality of alpha-hydroxycarboxylic acids were protected with alkyl or acyl groups and then formation of acid chloride followed by the reaction with trialkylphosphite furnished protected alpha-keto-beta-hydroxyphosponates. Nucleophilic addition reactions were applied to these compounds to obtain quaternary alcohols with phosphonate functionality. The addition reactions were tried...

Citation Formats

A. Akdağ and S. D. Worley, “Oxidation of organic sulfides by N-halamine compounds,” PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, pp. 1525–1533, 2007, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/56291.