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Silver(I)‐Mediated Dual Cleavage of C–C and C–O Bonds in the Reaction of Diarylmethylenecyclopropanes with Tetrahydrofuran: Synthesis of 4‐(3‐Halobut‐3‐enyloxy)butyl 2,2,2‐Trifluoroacetate Derivatives
Author(s) -
Chen GenQiang,
Tang XiangYing,
Shi Min
Publication year - 2014
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201301262
Subject(s) - chemistry , tetrahydrofuran , electrophile , halogenation , reagent , medicinal chemistry , cleavage (geology) , bond cleavage , electrophilic aromatic substitution , electrophilic addition , organic chemistry , catalysis , geotechnical engineering , solvent , fracture (geology) , engineering
The reaction of methylenecyclopropanes (MCPs) with tetrahydrofuran (THF) proceed smoothly in the presence of AgOC(O)CF 3 and electrophilic halogenation reagents to give the corresponding 4‐(3‐halobut‐3‐enyloxy)butyl 2,2,2‐trifluoroacetate derivatives in moderate yields through dual cleavage of C–C and C–O bonds under mild conditions.