Journal of the American Chemical Society

Solvent-Promoted E2 Reaction Competing with SN2 Reaction and Stepwise Solvolytic Elimination and Substitution Reactions

Q Meng, A Thibblin

文献索引：Meng, Qingshui; Thibblin, Alf Journal of the American Chemical Society, 1995 , vol. 117, # 37 p. 9399 - 9407

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被引用次数: 20

摘要

Abstract: Solvolysis of 9-(lX-ethyl) fluorene (1-X, X= I, Br, C1, OTs, or OBs) in 25 vol% acetonitrile in water gives the elimination products 9-(1-ethy1idene) fluorene (3) and 9- vinylfluorene (2) and the substitution products 9-(1-hydroxyethy1) fluorene (1-OH) and 9-(1- acetamidoethy1) fluorene (1-NHCOMe). The iodide (1-1) and the bromide (1-Br) yield 3 as the main product by a solvent-promoted concerted E2 reaction (J. Am. Chem. SOC. 1995, ...