SYNTHESIS OF 2,5-DIARYL-3-HALOFURANS VIA REGIOSELECTIVE RING-CLEAVAGEOF ARYL 3-ARYL-2,2-DIHALOCYCLOPROPYL KETONES

Authors
TANABE Y WAKIMURA K NISHII Y MUROYA Y
Citation
Y. Tanabe et al., SYNTHESIS OF 2,5-DIARYL-3-HALOFURANS VIA REGIOSELECTIVE RING-CLEAVAGEOF ARYL 3-ARYL-2,2-DIHALOCYCLOPROPYL KETONES, Synthesis, (3), 1996, pp. 388
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Synthesis → ACNP
ISSN journal
00397881
Issue
3
Year of publication
1996
Database
ISI
SICI code
0039-7881(1996):3<388:SO2VRR>2.0.ZU;2-T
Abstract
Several aryl 3-aryl-2,2-dihalocyclopropyl ketones were converted to 2, 5-diaryl-3-halofurans in the presence of aluminum chloride via regiose lective gem-dihalocyclopropane ring-cleavage. Friedel-Crafts acylation of substituted benzenes with 3-aryl-2,2-dihalocyclopropanecarbonyl ch lorides followed by this furan formation also proceeded in a one-pot m anner. For functionalization, bromine on a furan ring was easily repla ced by methyl and carboxyl groups; lithiation using butyllithium follo wed by the treatment with iodomethane and carbon dioxide, respectively .