Nucleophilic Reactivity of the Carbon-Carbon Double Bond. I. Solvolytic Ring Closure of 2-(Δ3-Cyclopentenyl) ethyl and 1-(Δ3-Cyclopentenyl)-2-propyl …

PD Bartlett, S Bank, RJ Crawford…

文献索引：Bartlett,P.D. et al. Journal of the American Chemical Society, 1965 , vol. 87, # 6 p. 1288 - 1297

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被引用次数: 28

摘要

The double bond in 2-(A3-cyclopentenyl) ethyl tosylate and p-nitrobenzenesulfonate participates directly in the solvolysis of these esters, as shown not only by the direct formation of exo-norbornjJl acetate as the product in acetic acid, but also by rate ratios from 5.8 in 50% aqueous ethanol to 640 in formic acid as the cyclopentenylethyl ester is compared with its saturated cyclopentylethyl analog. No 0'8 scrambling occurs when the p ...