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Furan derivatives. II. Synthesis and some properties of α,β-unsaturated sulfones of the 5-nitrofuran series

A. Jurášek, J. Kováč, and J. Abrahám

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

Abstract: Derivatives of l-(5-nitro-2-furyl)-l-methylsulfonyl-2-(4-X-phen3rl)ethylene (A), where X is H, N(CH₃)₂, I, CN, and NO₂ were synthesized by the condensation of 5-nitrofurfuryl methyl sulfone (S_m) with 4-substituted benzaldehydes. Similar condensation of S_m with 5-substituted 2-furaldehydes gave the derivatives of l-(5-nitro-2-furyl)-l-methylsulfonyl-2-(5-X-furyl)- ethylene (B), where X is H, CH₃ , Br, I, and COOCH₃. Condensation of 5-nitrofurfuryl phenyl sulfone (S_p) with 5-X-2-furaldehydes afforded the derivatives of l-(5-nitro-2-furyl)-l-phenylsulfonyl-2-(5-X-furyl)ethylene (C), where X is H, CH₃ , SCH₃, Br, I, COOCH₃, and NO₂ . Based on their i.r. and u.v. spectra the structure of the synthesized substances is discussed.

Full paper in Portable Document Format: 282a262.pdf

Chemical Papers 28 (2) 262–269 (1974)