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Hammett correlation of nornicotine analogues in the aqueous aldol reaction: Implications for green organocatalysis

Academic Article
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Overview

authors

  • Rogers, C. J.
  • Dickerson, Tobin
  • Brogan, A. P.
  • Janda, Kim

publication date

  • April 2005

journal

  • Journal of Organic Chemistry  Journal

abstract

  • [reaction: see text] A series of meta- and para-substituted 2-arylpyrrolidines were synthesized and examined for their ability to catalyze an aqueous aldol reaction under buffered conditions. Kinetic analysis of arylpyrrolidine-catalyzed reactions displayed a linear Hammett correlation with rho = 1.14 (R(2) = 0.996), indicating that the reaction is accelerated by electron-withdrawing aryl rings. These results show promise for the development of a synthetically viable aqueous organo-catalyst.

subject areas

  • Catalysis
  • Indicators and Reagents
  • Kinetics
  • Molecular Structure
  • Nicotine
  • Pyrrolidines
  • Stereoisomerism
  • Water
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Identity

International Standard Serial Number (ISSN)

  • 0022-3263

Digital Object Identifier (DOI)

  • 10.1021/jo050161r

PubMed ID

  • 15845010
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Additional Document Info

start page

  • 3705

end page

  • 3708

volume

  • 70

issue

  • 9

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