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Reductions with NADH models. 3. The high reactivity of Hantzsch amides

✍ Scribed by Gelbard, Georges; Lin, Jian; Roques, Nathalie


Book ID
118054366
Publisher
American Chemical Society
Year
1992
Tongue
English
Weight
674 KB
Volume
57
Category
Article
ISSN
0022-3263

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Abslract : The regioselectivity of the reduction of the cyclic enamide 2a with an NADH model compound was established using a deuterated model. The geometry of the substrate seems to play a fundamental role since cyclic derivatives 2a and 2d were reduced and non cyclic derivatives 2b and 2c were not

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The reaction kinetics of the reactions of Hantzsch esters (HEH) and Hantzsch 4-aryl-1,4-dihydropyridines (4aryl-HEH) with the tropylium cation as a formal hydride acceptor were investigated. The observed kinetic isotope effect (KIE, k H /k D ), using HEH and 4,4-d 2 -HEH as substrates, was 4.16, sug