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Molecules 2012, 17(5), 4782-4790; doi:10.3390/molecules17054782

Article

Preparation of S_RN1-Type Coupling Adducts from Aliphatic gem-Dinitro Compounds in Ionic Liquids

Akio Kamimura*  and Seiichi Toyoshima

Department of Applied Molecular Bioscience, Graduate School of Medicine, Yamaguchi University, Ube 755-8611, Japan

* Author to whom correspondence should be addressed.

Received: 29 February 2012; in revised form: 2 April 2012 / Accepted: 12 April 2012 / Published: 25 April 2012

(This article belongs to the Special Issue Ionic Liquids)

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Abstract: S_RN1-type coupling adducts are readily prepared by the reaction between a-sulfonylesters or a-cyanosulfones and gem-dinitro compounds in ionic liquids. The reactions progress smoothly and recovered ionic liquids can be used for several iterations, as long as they are washed with water to remove alkali metallic salts. The reaction rate is slower than the corresponding S_RN1 reaction in DMSO, but no acceleration on irradiation or no inhibition in the presence of m-DNB are observed.

Keywords: S_RN1-type adducts; ionic liquids; nitro compounds; kinetics

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