Osmium(VIII)-Catalyzed Oxidation of Pentamethylene Sulfide

Journal Title, Volume, Page:

Transition Metal Chemistry February 2004, Volume 29, Issue 1, pp 91-95

Year of Publication:

2004

Link:

http://link.springer.com/article/10.1023%2FB%3ATMCH.0000014491.58183.6d

Authors:

Mohammed M. Al-Subu

Department of Chemistry, Faculty of Science, An-Najah National University, Nablus, Palestine

Current Affiliation:

Department of Chemistry, Faculty of Science, An-Najah National University, Nablus, Palestine

[email protected]

Preferred Abstract (Original):

Although pentamethylene sulfide (tetrahydrothiopyran) lacks acidic hydrogen, Os^VIII has been found to catalyze its oxidation by alkaline K₃Fe(CN)₆ to produce 3-hydroxypentamethylene sulfide as the only product. The kinetics reveal first-order dependence on ferricyanide and Os^VIII, and zero order on pentamethylene sulfide and OH⁻. The effects of introduced electrolytes, K₄Fe(CN)₆, relative permittivity and temperature have also been studied. On the basis of kinetic evidence, a mechanism that involves anation of the osmium catalyst (sulfide/water interchange) followed by intramolecular proton abstraction, followed by an electron transfer step has been proposed and discussed.

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Osmium(VIII)-Catalyzed Oxidation of Pentamethylene Sulfide