Regioselective synthesis of dihydrofurans from 2, 2-dibromo 1, 3-diones and olefins using copper

J Yoshida, S Yano, T Ozawa…

Index: Yoshida, Jun-ichi; Yano, Shinji; Ozawa, Tadahiro; Kawobata, Nariyoshi Journal of Organic Chemistry, 1985 , vol. 50, # 19 p. 3467 - 3473

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Citation Number: 36

Abstract

2, 2-Dibromo 1, 3-diones reacted with copper powder and olefin to give 2, 3-dihydrofuran derivatives in a highly regioselective fashion. Acetylenes and 1, 3-dienes also reacted with 2, e-dibromo 1, 3-diones and copper to afford furan derivatives and 2-vinyl-2, 3-dihydrofuran derivatives, respectively. In benzene copper was converted into copper (1) bromide during the course of reaction, whereas in Me2S0 copper was converted into copper (I1) bromide. ...