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Furan derivatives. CLI. Synthesis of 2-Y-3-(5-methylthio- and 5-methylsulfonyl-2-furyl)acrylonitriles and kinetics of their reaction with nucleophilic reagents

V. Knoppová, R. Kada, and J. Kováč

Department of Organic Chemistry, Slovak Technical University, 880 37 Bratislava

 

Abstract:  2-Cyano-3-(5-methylthio- and 5-methylsulfonyl-2-furyl)acrylonitriles and methyl 2-cyano-3-(5-methylthio- and 5-methylsulfonyl-2-furyl)acrylates were prepared as model substances to study kinetics of nucleophilic replacement with secondary cyclic amines. Effects on the reaction rate of three different nucleophiles and of the electron-withdrawing group CH=C(Y)CN at position 2 of the furan ring were investigated. The results obtained were compared with kinetic data of the SN reaction of 5-(4-X-phenylsulfonyl- or -phenyl thio)-2-furfurylidenemalononitriles.

Full paper in Portable Document Format: 344a556.pdf

 

Chemical Papers 34 (4) 556–560 (1980)

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