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The steric structure and solvent effect of 6,6-dialkylfulvenes in reaction with α-naphthyllithium is studied. It is found for the first time that organolithium causes fulvenes to undergo reductive coupling reaction. In ether-THF, α-naphthyllithium also adds on the exo-cyclic double bond on 6, 6-dimethyl-, diethyl-and 6-methyl-6-ethylfulvene and abstracts α-hydrogen from the side chain of the fulvene in competition with the reduction and reductive coupling reaction. The reductive coupling reaction takes place when α-naphthyllithium reacts with 6-methyl-6-n-propyl-, -n-butyl-, and -i-butylfulvenes. There are various ways of activating 6, 6-polymethylene-fulvenes including tetra-, penta-, and hexamethylenefulvenes, all related with their structures. In ether-petroleum ether (1: 1), except that the 6, 6-tetramethylene-fulvenes undergoes α-hydrogen abstraction reaction, all the other 6, 6-dialkylfulvenes, 6, 6-penta- and hexamethylenefulvenes with α-naphthyllithium mainly undergo addition reaction.From 相似文献
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富烯与α-萘基锂反应的研究 总被引:2,自引:0,他引:2
本文研究了6,6-二烷基富烯与α-萘基锂反应的立体结构和溶剂效应。首次发现了富烯与有机锂的还原偶联反应。在乙醚-THF中α-萘基锂与6,6-二甲基、二乙基和甲基乙基富烯发生环外双键的加成、α-氢攫取、还原和还原偶联的竞争反应。与6-甲基-6-正丙基,正丁基,异丁基富烯发生还原偶联反应.与n=4,5,6的6,6-n亚甲基富烯分别进行α-氢攫取、还原和还原偶联反应.在1:1的乙醚-石油醚中,除6,6-四亚甲基富烯发生α-氢攫取外,其他所有富烯主要进行加成反应。利用上述反应合成一些新的取代和桥联双(环戊二烯基)钛、锆衍生物。 相似文献
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