Kinetics and mechanism of solvolysis of Precocene I 3, 4-oxide: change in rate-determining step and trapping of an intermediate in an epoxide solvolysis reaction

JM Sayer, SJ Grossman, KS Adusei-Poku…

Index: Sayer, J. M.; Grossman, S. J.; Adusei-Poku, K. S.; Jerina, D. M. Journal of the American Chemical Society, 1988 , vol. 110, # 15 p. 5068 - 5074

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Citation Number: 5

Abstract

Abstract: Solvolysis reactions of most highly reactive benzylic epoxides studied to date exhibit simple biphasic pH-rate profiles consisting of a hydronium ion dependent (kH) and a pH-independent (k,) region. In contrast, the pH-rate profile (extrapolated to zero buffer concentration) for the solvolysis of precocene I 3, 4-oxide (3, 4-dihydro-3, 4-epoxy-7- methoxy-2, 2-dimethyl-2~-benzo [b] pyran) to diols at 25 OC in 1: 9 dioxane-water, at ionic ...

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