preparation of srn1-type coupling adducts from aliphatic gem-dinitro compounds in ionic liquids从脂肪族化合物gem-dinitro srn1-type耦合加合物的制备离子液体.pdfVIP

Molecules 2012, 17, 4782-4790; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Preparation of SRN 1-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; E-Mail: ak10@yamaguchi-u.ac.jp; Tel./Fax: +81-836-859-231. Received: 29 February 2012; in revisedform: 2 April 2012 / Accepted: 12 April 2012 / Published: 25 April 2012 Abstract: SRN 1-type coupling adducts are readily prepared by the reaction between -sulfonylesters or -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 SRN 1 reaction in DMSO, but no acceleration on irradiation or no inhibition in the presence of m-DNB are observed. Keywords: SRN 1-type adducts; ionic liquids; nitro compounds; kinetics 1. Introduction The SRN 1 reaction is a unique reaction that proceeds via a single electron transfer process [1–3]. The reaction usually starts with a single electron transfer that generates a radical anion species, which then gives a radical species via cleavage of the anion radical. Then, the radical reacts with a coup