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Simple Approach to the Highly Stereoselective Synthesis of trans ‐1,2‐Cyclopropane Derivatives
Author(s) -
Zhang Hui,
Cao WeiGuo,
Ren ZhongJiao,
Chen Jie,
Sun RuShu,
Hu JiRong,
Qian JiaXian,
Deng HongMei
Publication year - 2007
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200790221
Subject(s) - cyclopropane , chemistry , stereoselectivity , malononitrile , chloroform , bromide , yield (engineering) , cyclopropanation , stereochemistry , proton nmr , medicinal chemistry , organic chemistry , catalysis , ring (chemistry) , materials science , metallurgy
Abstract In the presence of KF·2H 2 O, 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, 1 H NMR, 1 H‐ 1 H COSY and microanalysis. The relative configuration of product 3 was determined by 1 H‐ 1 H NOESY technique. The mechanism for the formation of product 3 was also proposed.