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Hydride‐Donor Abilities of 1,4‐Dihydropyridines: A Comparison with π Nucleophiles and Borohydride Anions
Authors:Dorothea Richter Dipl‐Chem  Herbert Mayr Prof Dr
Institution:Department Chemie und Biochemie, Ludwig‐Maximilians‐Universit?t München, Butenandtstrasse 5–13 (Haus F), 81377 München (Germany), Fax: (+49)?89‐2180‐77717 http://www.cup.uni‐muenchen.de/oc/mayr
Abstract:How are dihydropyridines like indoles? Both groups of compounds have similar nucleophilicity parameters N and are therefore suitable substrates for iminium‐catalyzed reactions of α,β‐unsaturated aldehydes. The N parameters of 1,4‐dihydropyridines were derived from the rates of hydride transfer reactions to benzhydrylium ions (see scheme).
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Keywords:iminium catalysis  kinetics  linear free‐energy relationships  nucleophilicity  reduction
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