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Spectroscopic Analysis of the Products of the Cycloaddition Reaction of 1‐Aryl‐2‐chlorocyclopropenes and Cyclopentadiene
Author(s) -
Ding MeiFang,
Lee ChuanChen,
Lin LianChun,
Lin ShawTao
Publication year - 2014
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.201300216
Subject(s) - chemistry , cyclopentadiene , cycloaddition , aryl , yield (engineering) , hexane , ionic liquid , methanol , medicinal chemistry , organic chemistry , catalysis , alkyl , materials science , metallurgy
The treatment of a series of 1‐aryl‐2,2‐dihalocyclopropanes with t ‐BuOK at −10 °C produces the corresponding 1‐aryl‐2‐halocyclopropenes, which react with cyclopentadiene to produce fairly good yield of [4+2]‐cycloaddition products with more than 90% of the endo ‐isomer. The higher yield obtained from hexane medium then from methanol and ionic liquid demonstrates that the reaction is a nonpolar process.