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A Convenient Synthesis of Fluorine‐Containing trans ‐1,2‐Cyclopropane Derivatives from Semistabilized Arsonium Ylides
Author(s) -
Wu Kaicheng,
Chen Yali,
Ma Xuyan,
Cao Weiguo,
Zhang Hui,
Chen Jie
Publication year - 2011
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.201180444
Subject(s) - chemistry , cyclopropane , fluorine , dichloromethane , stereoselectivity , cyclopropanation , aqueous solution , medicinal chemistry , organic chemistry , ring (chemistry) , catalysis , solvent
The fluorine‐containing trans ‐1,2‐cyclopropane derivatives 4ba – 4dd were synthesized from the fluorine‐containing electron‐deficient alkenes 3a – 3d with semistabilized arsonium ylides 2b – 2d , in biphasic system of dichloromethane‐50% aqueous sodium hydroxide, generated in situ from the corresponding arsonium salts 1b – 1d at room temperature in good yields with high stereoselectivity. The structure of fluorine‐containing trans ‐1,2‐cyclopropane derivatives were also studied.