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Revisiting Nucleophilic Substitution Reactions: Microwave-Assisted Synthesis of Azides, Thiocyanates, and Sulfones in an Aqueous Medium

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Yuhong Ju,^† Dalip Kumar,^‡ and Rajender S. Varma*^†

Clean Processes Branch, Sustainable Technology Division, National Risk Management Research Laboratory, U.S. Environmental Protection Agency, 26 West Martin Luther King Drive, MS 443, Cincinnati, Ohio 45268, and Chemistry Group, Birla Institute of Technology and Science, Pilani 333031, Rajasthan, India ju.yuhong@epa.gov; dalipk@bits-pilani.ac.in; varma.rajender@epa.gov

J. Org. Chem., 2006, 71 (17), pp 6697–6700

DOI: 10.1021/jo061114h

Publication Date (Web): July 28, 2006

†

U.S. Environmental Protection Agency.

‡

Birla Institute of Technology and Science.

To whom correspondence should be addressed. Tel: (+1-513) 487-2701. Fax: (+1-513) 569-7677.

Abstract

A practical, rapid, and efficient microwave (MW) promoted synthesis of various azides, thiocyanates, and sulfones is described in an aqueous medium. This general and expeditious MW-enhanced nucleophilic substitution approach uses easily accessible starting materials such as halides or tosylates in reaction with alkali azides, thiocyanates, or sulfinates in the absence of any phase-transfer catalyst, and a variety of reactive functional groups are tolerated.

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Published In Issue August 18, 2006
Received May 31, 2006

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Note

Revisiting Nucleophilic Substitution Reactions: Microwave-Assisted Synthesis of Azides, Thiocyanates, and Sulfones in an Aqueous Medium

Abstract

Tools

SciFinder Links

History

Recommend & Share

Related Content

Azides: their preparation and synthetic usesAzides: their preparation and synthetic uses

Peptidotriazoles on Solid Phase: [1,2,3]-Triazoles by Regiospecific Copper(I)-Catalyzed 1,3-Dipolar Cycloadditions of Terminal Alkynes to Azides

Aqueous N-Heterocyclization of Primary Amines and Hydrazines with Dihalides: Microwave-Assisted Syntheses of N-Azacycloalkanes, Isoindole, Pyrazole, Pyrazolidine, and Phthalazine Derivatives

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