Hammett correlation of nornicotine analogues in the aqueous aldol reaction: implications for green organocatalysis - PubMed (original) (raw)
. 2005 Apr 29;70(9):3705-8.
doi: 10.1021/jo050161r.
Affiliations
- PMID: 15845010
- DOI: 10.1021/jo050161r
Hammett correlation of nornicotine analogues in the aqueous aldol reaction: implications for green organocatalysis
Claude J Rogers et al. J Org Chem. 2005.
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.
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