- Bidentate Lewis acids for the activation of 1,2-diazines - A new mode of catalysis
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Bidentate Lewis acids were applied as catalysts for the inverse-electron-demand Diels-Alder (IEDDA) reaction of 1,2-diazines. The concept of catalysis is based on the coordination of the bidentate Lewis acid to both nitrogen atoms of the 1,2-diazine moiety, thereby reducing the electron density and lowering the energy of the LUMO. This should, according to frontier molecular orbital (FMO) theory, facilitate the cycloaddition step. This new concept was successfully applied to a variety of dienophiles and substituted phthalazine substrates. Careful investigations of the mechanism led to the isolation and characterization of key intermediates; all of which support the presented catalytic cycle. Copyright
- Kessler, Simon N.,Neuburger, Markus,Wegner, Hermann A.
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supporting information; experimental part
p. 3238 - 3245
(2011/07/08)
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- Lewis acid catalyzed inverse electron-demand diels-alder reaction of 1,2-diazines
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A systematic approach toward Lewis acid catalyzed inverse electron-demand Diels-Alder (IEDDA) reactions of 1,2-diazines is described. The general concept is first investigated by DFT calculations, supported by spectroscopic data, and finally proven in the experiment.
- Kessler, Simon N.,Wegner, Hermann A.
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supporting information; experimental part
p. 4062 - 4065
(2010/11/17)
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- Annulations Using Phosphonium Salts and Enolate Anions - A Direct Route to Naphthalenes
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Ketone enolates react with an aldehyde phosphonium salt to produce naphthalenes in a one-pot reaction.
- Kraus, George A.,Choudhury, Prabir K.
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- Intramolecular Reaction Of Nitroxide Radicals With Biradical Intermediates Generated From Aromatic Enediynes
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1,4-Dehydronaphthalene biradicals generated by thermolysis of aromatic enediynes can be trapped with the nitroxide radical TEMPO.The isolated products, however, are not the direct trapping products but 1,4-naphthoquinones resulting from the homolysis of N-O bonds of trapping products.
- Grissom, Janet Wisniewski,Gunawardena, Gamini U.
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p. 4951 - 4954
(2007/10/02)
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- AROMATIC ANNELATION. SYNTHESIS OF NAPHTHALENES.
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An efficient cationic cyclization reaction has been developed to prepare substituted naphthalenes.The method has been used to prepare a phenanthrene and will be useful for the synthesis of polynuclear aromatic hydrocarbons and C-glycosyl anthraquinones.
- Tius, Marcus A.,Gomez-Galeno, Jorge
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p. 2571 - 2574
(2007/10/02)
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