Journal
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
Volume 73, Issue 3, Pages 713-719Publisher
CHEMICAL SOC JAPAN
DOI: 10.1246/bcsj.73.713
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Various oxiranes reacted with carbon dioxide at 100 degrees C using lithium bromide as a catalyst under atmospheric pressure to afford the corresponding five-membered cyclic carbonates quantitatively. The rate of the reaction increased as the bulkiness of substituents on the oxirane ring was reduced or an electron-withdrawing group was introduced on the oxirane ring. The stereochemistry of the reaction of oxirane and carbon dioxide was retention without loss of optical purity. When substituted phenylethylene carbonates were reacted with benzylamine, the selectivity to afford secondary alcohol increased as the electron-withdrawing ability of the para-substituent increased.
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