Hammett Correlation of Nornicotine Analogues in the Aqueous Aldol Reaction: Implications for Green Organocatalysis
- 31 March 2005
- journal article
- research article
- Published by American Chemical Society (ACS) in The Journal of Organic Chemistry
- Vol. 70 (9) , 3705-3708
Abstract
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 ρ = 1.14 (R2 = 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 organocatalyst.Keywords
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