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Pure Appl. Chem., 1998, Vol. 70, No. 10, pp. 1993-2000

http://dx.doi.org/10.1351/pac199870101993

Reactivities and selectivities of free and metal-coordinated carbocations

Herbert Mayr, M. Patz, M. F. Gotta and A. R. Ofial

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  • Tandon Raman, Unzner Teresa, Nigst Tobias A., De Rycke Nicolas, Mayer Peter, Wendt Bernd, David Olivier R. P., Zipse Hendrik: Annelated Pyridines as Highly Nucleophilic and Lewis Basic Catalysts for Acylation Reactions. Chem. Eur. J. 2013, 19, 6435. <http://dx.doi.org/10.1002/chem.201204452>
  • Kiyooka Syun-ichi, Kaneno Daisuke, Fujiyama Ryoji: Intrinsic reactivity index as a single scale directed toward both electrophilicity and nucleophilicity using frontier molecular orbitals. Tetrahedron 2013, 69, 4247. <http://dx.doi.org/10.1016/j.tet.2013.03.083>
  • Forlani Luciano, Boga Carla, Mazzanti Andrea, Zanna Nicola: Trapping and Analysing Wheland-Meisenheimer σ Complexes, Usually Labile and Escaping Intermediates. Eur J Org 2012, 2012, 1123. <http://dx.doi.org/10.1002/ejoc.201101498>
  • Berionni Guillaume, Branca Mathieu, Pégot Bruce, Marrot Jérome, Kizilian Elyane, Goumont Régis: The N-Alkylation of Substituted 4-Tetrazolo[1,5-a]pyridines: Easy Access to a New Series of Electrophiles. Eur J Org Chem 2011, 2011, 5104. <http://dx.doi.org/10.1002/ejoc.201100595>
  • Lakhdar Sami, Terrier François, Vichard Dominique, Berionni Guillaume, El Guesmi Nizar, Goumont Régis, Boubaker Taoufik: The Diels-Alder Reaction of 4,6-Dinitrobenzofuroxan with 1-Trimethylsilyloxybuta-1,3-diene: A Case Example of a Stepwise Cycloaddition. Chemistry - A European Journal 2010, 16, 5681. <http://dx.doi.org/10.1002/chem.200903008>
  • Mayr Herbert, Patz Matthias, Gotta Matthias F., Ofial Armin R.: ChemInform Abstract: Reactivity and Selectivity of Free and Metal-Coordinated Carbocations. ChemInform 2010, 30, no. <http://dx.doi.org/10.1002/chin.199928310>
  • Buncel Erwin, Terrier François: Assessing the superelectrophilic dimension through σ-complexation, SNAr and Diels–Alder reactivity. Org Biomol Chem 2010, 8, 2285. <http://dx.doi.org/10.1039/b923983a>
  • El Guesmi Nizar, Boubaker Taoufik, Goumont Regis, Terrier François: The Ambident Reactivity of 2,4,6-Tris(trifluoromethanesulfonyl)anisole in Methanol: Using the SO2CF3 Group as a Tool to Reach the Superelectrophilic Dimension in σ-Complexation Processes. Chem Eur J 2009, 15, 12018. <http://dx.doi.org/10.1002/chem.200901123>
  • Shi Lei, Horn Markus, Kobayashi Shinjiro, Mayr Herbert: Carbocationic n-endo-trig Cyclizations. Chem Eur J 2009, 15, 8533. <http://dx.doi.org/10.1002/chem.200901246>
  • Maitlis Peter M., Zanotti Valerio: The role of electrophilic species in the Fischer–Tropsch reaction. Chem Commun 2009, 1619. <http://dx.doi.org/10.1039/b822320n>
  • Mayr Herbert, Ofial Armin R.: Do general nucleophilicity scales exist?. J Phys Org Chem 2008, 21, 584. <http://dx.doi.org/10.1002/poc.1325>
  • El Guesmi Nizar, Boubaker Taoufik, Goumont Régis, Terrier François: Electrophilicity of aromatic triflones in σ-complexation processes. Org Biomol Chem 2008, 6, 4041. <http://dx.doi.org/10.1039/b810273b>
  • Lakhdar Sami, Goumont Régis, Berionni Guillaume, Boubaker Taoufik, Kurbatov Sergey, Terrier François: Superelectrophilicity of the Nitroolefinic Fragment of 4-Nitrobenzodifuroxan in Michael-Type Reactions with Indoles: A Kinetic Study in Acetonitrile. Chem Eur J 2007, 13, 8317. <http://dx.doi.org/10.1002/chem.200700676>
  • Lakhdar Sami, Goumont R?gis, Terrier Fran?ois, Boubaker Taoufik, Dust Julian M., Buncel Erwin: Mayr electrophilicity predicts the dual Diels?Alder and ?-adduct formation behaviour of heteroaromatic super-electrophiles. Org Biomol Chem 2007, 5, 1744. <http://dx.doi.org/10.1039/b702060k>
  • Berger Stefan T. A., Seeliger Florian H., Hofbauer Florian, Mayr Herbert: Electrophilicity parameters for 2-benzylidene-indan-1,3-diones—a systematic extension of the benzhydrylium based electrophilicity scale. Org Biomol Chem 2007, 5, 3020. <http://dx.doi.org/10.1039/b708025e>
  • Denegri Bernard, Streiter André, Jurić Sandra, Ofial Armin R., Kronja Olga, Mayr Herbert: Kinetics of the Solvolyses of Benzhydryl Derivatives: Basis for the Construction of a Comprehensive Nucleofugality Scale. Chem Eur J 2006, 12, 1648. <http://dx.doi.org/10.1002/chem.200500845>
  • Berestneva Tatiana Klimova, García Marcos Martínez, Ortiz-Frade Luis, Ortega Simon Hernández, Toscano Ruben A., Klimova Elena: Synthesis, structures and some chemical and electrochemical properties of E-1,2-diferrocenyl-3-methylthioprop-2-enone and its ketals. J Organomet Chem 2006, 691, 2872. <http://dx.doi.org/10.1016/j.jorganchem.2006.02.024>
  • Kempf Bernhard, Mayr Herbert: Rates and Equilibria of the Reactions of Tertiary Phosphanes and Phosphites with Benzhydrylium Ions. Chem Eur J 2005, 11, 917. <http://dx.doi.org/10.1002/chem.200400696>
  • Dilman Alexander D., Mayr Herbert: Nucleophilic Reactivities of Silyl Ketene Acetals and Silyl Enol Ethers Containing (C6F5)3SiO and (C6H5)3SiO Groups. Eur J Org Chem 2005, 2005, 1760. <http://dx.doi.org/10.1002/ejoc.200400706>
  • Remennikov Grigoriy Ya., Kempf Bernhard, Ofial Armin R., Polborn Kurt, Mayr Herbert: 5-Methoxyfuroxano[3,4-d]pyrimidine: a highly reactive neutral electrophile. J Phys Org Chem 2003, 16, 431. <http://dx.doi.org/10.1002/poc.606>
  • Lucius Roland, Loos Robert, Mayr Herbert: Kinetische Untersuchungen von Carbokation-Carbanion-Kombinationen: Schlüssel zu einem allgemeinen Modell polarer organischer Reaktivität. Angew Chem 2002, 114, 97. <http://dx.doi.org/10.1002/1521-3757(20020104)114:1<97::AID-ANGE97>3.0.CO;2-4>
  • Lucius Roland, Loos Robert, Mayr Herbert: Kinetic Studies of Carbocation-Carbanion Combinations: Key to a General Concept of Polar Organic Reactivity. Angewandte Chemie-Int Ed 2002, 41, 91. <http://dx.doi.org/10.1002/1521-3773(20020104)41:1<91::AID-ANIE91>3.0.CO;2-P>
  • Fichtner Claudia, Remennikov Grigoriy, Mayr Herbert: Kinetics of the Reactions of Flavylium Ions with π-Nucleophiles. Eur J Org Chem 2001, 2001, 4451. <http://dx.doi.org/10.1002/1099-0690(200112)2001:23<4451::AID-EJOC4451>3.0.CO;2-F>
  • Lucius Roland, Mayr Herbert: Konstante Selektivitätsbeziehungen bei Additionsreaktionen von Carbanionen. Angew Chem 2000, 112, 2086. <http://dx.doi.org/10.1002/1521-3757(20000602)112:11<2086::AID-ANGE2086>3.0.CO;2-T>
  • Goldfuss Bernd, Knochel Paul, Bromm Lars O., Knapp Kolja: C-H-Aktivierung durch direkte Boran-Kohlenwasserstoff-Dehydrierung: kinetische und thermodynamische Aspekte. Angew Chem 2000, 112, 4302. <http://dx.doi.org/10.1002/1521-3757(20001117)112:22<4302::AID-ANGE4302>3.0.CO;2-4>
  • Goldfuss Bernd, Knochel Paul, Bromm Lars O., Knapp Kolja: C−H Activation by Direct Borane–Hydrocarbon Dehydrogenation: Kinetic and Thermodynamic Aspects. Angew Chem 2000, 39, 4136. <http://dx.doi.org/10.1002/1521-3773(20001117)39:22<4136::AID-ANIE4136>3.0.CO;2-F>
  • Böttger Guido M., Fröhlich Roland, Würthwein Ernst-Ulrich: Electrophilic Reactivity of a 2-Azaallenium and of a 2-Azaallylium Ion. Eur J Org Chem 2000, 2000, 1589. <http://dx.doi.org/10.1002/(SICI)1099-0690(200004)2000:8<1589::AID-EJOC1589>3.0.CO;2-T>