The Journal of organic chemistry

Reaction of Lithium Diethylamide with an Alkyl Bromide and Alkyl Benzenesulfonate: Origins of Alkylation, Elimination, and Sulfonation

L Gupta, A Ramírez, DB Collum

文献索引：Gupta, Lekha; Ramirez, Antonio; Collum, David B. Journal of Organic Chemistry, 2010 , vol. 75, # 24 p. 8392 - 8399

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被引用次数: 6

摘要

A combination of NMR, kinetic, and computational methods are used to examine reactions of lithium diethylamide in tetrahydrofuran (THF) with n-dodecyl bromide and n-octyl benzenesulfonate. The alkyl bromide undergoes competitive SN2 substitution and E2 elimination in proportions independent of all concentrations except for a minor medium effect. Rate studies show that both reactions occur via trisolvated-monomer-based ...