Calixarene-Catalyzed Generation of Dichlorocarbene and Its Application to Organic Reactions: The Catalytic Action of Octopus-Type Calix[6]arene
- 1 March 1994
- journal article
- Published by Oxford University Press (OUP) in Bulletin of the Chemical Society of Japan
- Vol. 67 (3) , 792-799
- https://doi.org/10.1246/bcsj.67.792
Abstract
The dichlorocarbene generation reaction from CHCl3 and solid KOH in CH2Cl2 was catalyzed by the p-t-butylcalix[6]arene derivative 1 which bears six 3,6,9-trioxadecyl substituents on the phenolic oxygens. Dichlorocarbene generated by this method reacted efficiently with alkenes and amides to give dichlorocyclopropane derivatives and nitriles, respectively, in high yields. The reaction with alkadiene having isolated double bonds gave mixtures of the mono- and bis-dichlorocarbene adducts, but the monoadduct formation always predominated. The catalytic action of the calixarene and the reactivity features of dichlorocarbene generated by the above procedure are discussed on the basis of kinetic measurements. They are also compared with those of the 18-crown-6-catalyzed reactions.This publication has 13 references indexed in Scilit:
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