New odorless method for the Corey-Kim and Swern oxidations utilizing dodecyl methyl sulfide (Dod-S-Me)
Shin-Ichi Ohsugi, Kiyoharu Nishide, Keiji Oono, Kazunori Okuyama, Masato Fudesaka, Sumiaki Kodama and Manabu Node*
*Kyoto Pharmaceutical University, Misasagi, Yamashina, Kyoto 607-8414,
Japan, Email: node
mb.kyoto-phu.ac.jp
S.-I. Ohsugi, K. Nishide, K. Oono, K. Okuyama, M. Fudesaka, S. Kodama, M. Node, Tetrahedron, 2003, 59, 8393-8398.
DOI: 10.1016/j.tet.2003.08.055
Abstract
Dodecyl methyl sulfide is an odorless alternatives to dimethyl sulfide in Swern and Corey-Kim Oxidations. New green chemistry methods for the Corey-Kim reaction utilizing Dod-S-Me and common solvents instead of dichloromethane are described.
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Details
The document describes the development of an odorless method for the Corey–Kim and Swern oxidations using dodecyl methyl sulfide (Dod-S-Me) as an alternative to the foul-smelling dimethyl sulfide (DMS). The research, conducted by Shin-ichi Ohsugi and colleagues, aims to improve green chemistry practices by eliminating the malodorous nature of traditional reagents. Dod-S-Me was synthesized and tested, showing it to be odorless due to its lower volatility compared to shorter-chain sulfides. The new Corey–Kim oxidation method using Dod-S-Me was optimized, yielding high results in both dichloromethane and toluene solvents. Additionally, the Swern oxidation was adapted using dodecyl methyl sulfoxide, a derivative of Dod-S-Me, which also proved to be effective and odorless. These methods were tested on various alcohols, yielding excellent results without the production of offensive odors. The document highlights the potential of these odorless reagents to enhance laboratory conditions and industrial applications, aligning with green chemistry principles. Further studies are ongoing to explore additional applications of these odorless sulfides and sulfoxides.
Dod-S-Me and Methyl 6-Morpholinohexyl Sulfide (MMS) as New Odorless Borane Carriers
P. K. Patra, K. Nishide, K. Fuji, M. Node, Synthesis, 2004, 1003-1006.
A practical improvement of odorless Corey-Kim and Swern oxidations
K. Nishide, P. K. Patra, M. Matoba, K. Shanmugasundaram, M. Node, Green Chem., 2004, 6, 142 - 146. DOI: 10.1039/b312849k
Key Words
Corey-Kim Oxidation, Swern Oxidation, Green Chemistry
ID: J72-Y2003-810
