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Competing radical, carbanion, and carbene pathways in the reactions of hindered primary alkyl halides with lithium dialkylamides

…, B Park, GS Patil, K Gadru, R Gurumurthy

文献索引:Ashby, E. C.; Park, B.; Patil, G. S.; Gadru, K.; Gurumurthy, R. Journal of Organic Chemistry, 1993 , vol. 58, p. 424 - 437

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被引用次数: 31

摘要

A variety of methods were utilized to study the mechanism of reaction of 6-iodo-5, 5-dimethyl- 1-hexene and its bromo, chloro, and tosylate derivatives with LDA and several other lithium dialkylamides. In the reaction of 6-iodo-5, 5-dimethyl-l-hexene with LDA in THF, radical, carbanion, and carbene pathways occurred simultaneously. However, when the corresponding bromide was allowed to react with LDA, the radical pathway was minor and ...

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