By Daniela Kampen, Corinna M. Reisinger, Benjamin List (auth.), Benjamin List (eds.)
Kerstin Etzenbach-Effers, Albrecht Berkessel: Non-Covalent Organocatalysis in response to Hydrogen Bonding: Elucidation of response Paths by means of Computational Methods.- Petri M. Pihko, Inkeri Majander, and Anniina Erkkilä: Enamine Catalysis.- Jennifer L. Moore, Tomislav Rovis: Lewis Base Catalysts 6: Carbene Catalysts.- Amal Ting, Jennifer M. Goss, Nolan T. McDougal, and Scott E. Schaus: Brønsted Base Catalysts.- O. Andrea Wong, Yian Shi: Chiral Ketone and Iminium Catalysts for Olefin Epoxidation.- Alan C. Spivey, Stellios Arseniyadis: Amine, Alcohol and Phosphine Catalysts for Acyl move Reactions.- John B. Brazier, Nicholas C.O. Tomkinson: Lewis Base Catalysts 2 Secondary and first Amine Catalysts for Iminium Catalysis.- Oksana Sereda, Sobia Tabassum, and René Wilhelm: Lewis Acid Organocatalysts.- Daniela Kampen , Corinna M. Reisinger , and Benjamin checklist: Chiral Bronsted Acids for C Organocatalysis.-
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1 The Structure of the Amine and the Resulting Enamine In general, the most nucleophilic enamines are those where the nitrogen lone pair is most effectively delocalized. This requires effective overlap of the lone pair with the C = C p bond and maximum flattening (sp2 hybridization) of the enamine nitrogen. The structure of the amine component has a profound influence on the propensity to p-p delocalization. As an example, enamines derived from cyclic fivemembered ring amines, such as pyrrolidine, are more than thousand times more nucleophilic than those derived from six-membered ring amines.
14 Stationary-point structures for the epoxidation of ethene with hydrogen peroxide in the absence and in the presence of one molecule of HFIP, optimized at RB3LYP/6-31 + G(d,p) (selected bond lengths in Å; RB3LYP/6-311++G(d,p) results in parentheses) 20 K. Etzenbach-Effers and A. 15). 823 Å) cooperatively increases the hydrogen bond donor ability of the alcohol molecule which activates the leaving OH-group. By this hydrogen bond pattern, a polarization of the O–O bond is achieved (the donated and accepted hydrogen bonds are not equal in length and angle), and an electron deficient oxygen is generated, ready for electrophilic attack on the olefinic double bond.
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