Design of new odorless and thermally-stable sulfides and their application to Swern oxidation

ORGN 131

Xun He, and Tak Hang Chan, Department of Chemistry, McGill University, 801 Sherbrooke Street, West, Montreal, QC H3A 2K6, Canada
The oxidation of alcohols to aldehydes and ketones is an important transformation in organic chemistry. Swern oxidation reaction is one of the efficient methods, which have been extensively used in organic synthetic research and industry. The original combination of oxidizing reagents involves the use of dimethylsulfoxide (DMSO) which is reduced into dimethylsulfide which is toxic, volatile and gives a strong stench. We have synthesized a new class of odorless, non-volatile and thermally-stable sulfides via an environmentally-benign process. The non-volatile and thermally-stable characteristics of ionic liquids have been successfully grafted to the sulfides. Their corresponding sulfoxides can be used effectively for the oxidation of alcohols into aldehydes and ketones under mild Swern oxidation conditions. The sulfides, after reactions, were easily recovered and recycled for four times to give oxidation products in high yield without obvious loss of activities.


New Reactions and Methodology, Materials, Total Synthesis, Process R&D
8:00 PM-10:00 PM, Sunday, 28 August 2005 Washington DC Convention Center -- Hall A, Poster

8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005