Elsevier

Tetrahedron Letters

Volume 38, Issue 27, 7 July 1997, Pages 4787-4790
Tetrahedron Letters

Evidence of a stepwise acyl-transfer reaction mechanism: Nonlinear Hammett plots for reactions of p-nitrophenyl substituted benzoates with hydroxide and p-chlorophenoxide

https://doi.org/10.1016/S0040-4039(97)01033-2Get rights and content

Abstract

The Hammett plots obtained for the title reactions exhibit a break, i.e. ϱacyl values decrease from 2.21∼2.44 to 1.45∼1.52 as the acyl substituent becomes a strong electron withdrawing group (σ >0.6). Such a break in the Hammett plots is suggestive of a change in the reaction mechanism and strong evidence of a stepwise mechanism for the acyl-transfer reaction.

Nonlinear Hammett plots obtained in the title reactions support a stepwise acyl-transfer reaction mechanism.

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References (18)

  • E. Buncel et al.

    J. Am. Chem. Soc.

    (1989)
  • M.J. Pregel et al.

    J. Am. Chem. Soc.

    (1991)
  • E.J. Dunn et al.

    Can. J. Chem.

    (1989)
  • D.S. Kwon et al.

    Bull. Korean Chem. Soc.

    (1990)
  • S. Ba-Saif et al.

    J. Am. Chem. Soc.

    (1987)
  • P. D'Rozario et al.

    J. Am. Chem. Soc.

    (1984)
  • N. Bourne et al.

    J. Am. Chem. Soc.

    (1988)
  • A.C. Hengge et al.

    J. Am. Chem. Soc.

    (1994)
  • A.C. Hengge et al.

    J. Am. Chem. Soc.

    (1994)
There are more references available in the full text version of this article.

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