Kinetic and thermodynamic barriers to carbon and oxygen alkylation of phenol and phenoxide ion by the 1-(4-methoxyphenyl) ethyl carbocation

…, MM Toteva, HA Garth, JP Richard

Index: Tsuji, Yutaka; Toteva, Maria M.; Garth, Heather A.; Richard, John P. Journal of the American Chemical Society, 2003 , vol. 125, # 50 p. 15455 - 15465

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Citation Number: 15

Abstract

Rate constant ratios for addition of the three nucleophilic sites of phenol to the 1-(4- methoxyphenyl) ethyl carbocation (1+) in 50/50 (v/v) trifluoroethanol/water were determined from the relative yields of the three phenol adducts, and absolute rate constants were determined from product rate constant ratios for addition of phenol and azide ion to 1+ using k az= 5× 109 M-1 s-1 for the diffusion-limited reaction of azide ion. A selectivity of 230: 20: ...