Hyperaromatic stabilization of arenium ions: acid-catalyzed dehydration of 2-substituted 1, 2-dihydro-1-naphthols

…, D Coyne, RAM O'Ferrall

文献索引：Kudavalli, Jaya Satyanarayana; Coyne, Dara; O'Ferrall, Rory A. More Journal of Organic Chemistry, 2012 , vol. 77, # 1 p. 563 - 572

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被引用次数: 6

摘要

Rate constants for acid-catalyzed dehydration of cis-2-substituted 1, 2-dihydro-naphthols are well correlated by the Taft relationship log k=− 0.49–8.8 σI, with minor negative deviations for OH and OMe. By contrast the trans substituents show a poor correlation with σI and in most cases react more slowly than their cis isomers. The behavior is consistent with rate- determining formation of a 2-substituted carbocation (naphthalenium ion) intermediate ...