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- W1509713672 abstract "Abstract The acetolysis of 3-(Δ 2 -cyclohexenyl)propyl p -nitrobenzenesulfonate ( 11 ) is 1·64 times as fast as that of its saturated analog, the 3-cyclohexylpropyl ester; it leads to a mixture including 18·9% of bicyclic products, which consist of olefins (3 or 4) and acetate (2) in the ratio of 1·67 to 1. The product is closely related in composition to that obtained 7 by acetolysis of the toluenesulfonate ( 14 ) of 9-bicylo(3.3.1)nonanol, except for a threefold lower proportion of olefins (characteristics of the π route) and greater stereospecificity in the acetates. The acetolysis of trans -2-(2-vinylcyclopentyl)ethyl p -nitrobenzenesulfonate ( 12 ) is only 95% as fast as the saturated standard, and leads to 95% of unrearranging acetate, 5% of equatorial trans -4-hydrindyl acetate, and no olefins. The isomeric p -nitrobenzenesulfonate ( 13 ) of cis -2-(2-vinylcyclopentyl) ethanol undergoes acetolysis at a rate 5·78 times that of the saturated standard. The product is 76% bicyclic and containts four hexahydroindenes and four hydrindyl acetates in the olefin/acetate ratio of 0·39, twelve times lower than that in the σ route from 14 . The solvolysis rates are rationalized in terms of the conformational barriers to be surmounted in the formation of the transition state, and are correlated with the fractions of bicyclic product formed. In line with earlier work, the olefin/acetate ratio in the product is regarded as an indication of the relative involvement of classical ion pairs in the reaction sequence, which is always less in the π route than in the σ route for reasons which are discussed. Differences in product compositions also require the occurrence of bridged ion pairs with different properties in the several cases." @default.
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- W1509713672 title "Nucleophilic reactivity of the carbon-carbon double bond—V" @default.
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