Simple Approach to the Highly Stereoselective Synthesis of trans-1,2-Cyclopropane Derivatives
Hui Zhang
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorWei-Guo Cao
Department of Chemistry, Shanghai University, Shanghai 200444, China
State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorZhong-Jiao Ren
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorJie Chen
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorRu-Shu Sun
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorJi-Rong Hu
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorJia-Xian Qian
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorHong-Mei Deng
Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, China
Search for more papers by this authorHui Zhang
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorWei-Guo Cao
Department of Chemistry, Shanghai University, Shanghai 200444, China
State Key Laboratory of Organometallic Chemistry, Chinese Academy of Sciences, Shanghai 200032, China
Search for more papers by this authorZhong-Jiao Ren
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorJie Chen
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorRu-Shu Sun
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorJi-Rong Hu
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorJia-Xian Qian
Department of Chemistry, Shanghai University, Shanghai 200444, China
Search for more papers by this authorHong-Mei Deng
Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, China
Search for more papers by this authorAbstract
In the presence of KF·2H2O, furoylmethyltriphenylarsonium bromide (1a) or thienoylmethyltriphenylarsonium bromide (1b) reacted with 2-[(un)substituted benzylidene]malononitrile (2) in chloroform at room temperature to give trans-3,3-dicyano-1-furoyl-2-[(un)substituted phenyl]cyclopropane (3a) or trans-3,3-dicyano-1-thienoyl-2-[(un)substituted phenyl]cyclopropane (3b) respectively in good yield with high stereoselectivity. The structures of product 3 were confirmed by IR, MS, 1H NMR, 1H-1H COSY and microanalysis. The relative configuration of product 3 was determined by 1H-1H NOESY technique. The mechanism for the formation of product 3 was also proposed.
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