Revisiting classical nucleophilic substitutions in aqueous medium: Microwave-assisted synthesis of alkyl azides

ORGN 197

Rajender S. Varma, Varma.Rajender@epa.gov1, Yuhong Ju, Ju.Yuhong@epa.gov1, and Dalip Kumar2. (1) Sustainable Technology Division, National Risk Management Research Laboratory, U. S. Environmental Protection Agency, 26 West Martin Luther King Drive, MS 443, Cincinnati, OH 45268, (2) Department of Chemistry, Birla Institute of Technology and Science, Pilani, Rajasthan, India
An efficient and clean synthesis of alkyl azides using microwave (MW) radiation is described in aqueous medium by reacting alkyl halides or tosylates with alkali azides. This general and expeditious MW-enhanced approach to nucleophilic substitution reactions is applicable to the formation alkyl thiocyanides with added advantage that various functional groups such as ester, carboxylic acid, carbonyl and hydroxyl etc. are tolerated under mild reaction conditions that does not require the use of a phase transfer reagent. Our exploration of this catalyst-free strategy to accomplish MW-assisted one-pot 1,3-dipolar cycloaddition reaction of alkynes with in situ generated alkyl azides will be discussed.

 

New Reactions and Methodology
8:00 AM-12:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- C301, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006