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Pure Appl. Chem., 1980, Vol. 52, No. 10, pp. 2283-2302

http://dx.doi.org/10.1351/pac198052102283

Cycloaddition mechanism and the solvent dependence of rate

R. Huisgen

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  • Bekhradnia Ahmad Reza, Arshadi Sattar, Siadati Seyed Amir: 1,3-Dipolar cycloaddition between substituted phenyl azide and 2,3-dihydrofuran. Chem. Pap. 2014, 68, 283. <http://dx.doi.org/10.2478/s11696-013-0440-7>
  • Tasdelen Mehmet Atilla, Yagci Yusuf: Lichtinduzierte Klickreaktionen. Angew. Chem. 2013, 125, 6044. <http://dx.doi.org/10.1002/ange.201208741>
  • Tasdelen Mehmet Atilla, Yagci Yusuf: Light-Induced Click Reactions. Angew. Chem. Int. Ed. 2013, 52, 5930. <http://dx.doi.org/10.1002/anie.201208741>
  • Cruchter Thomas, Harms Klaus, Meggers Eric: Strain-Promoted Azide-Alkyne Cycloaddition with Ruthenium(II)-Azido Complexes. Chem. Eur. J. 2013, 19, 16682. <http://dx.doi.org/10.1002/chem.201302502>
  • Khalfina Irina A., Vlasov Vladislav M.: Enthalpy-Entropy Correlations in Reactions of Aryl Benzoates with Potassium Aryloxides in Dimethylformamide. Int. J. Chem. Kinet. 2013, 45, 266. <http://dx.doi.org/10.1002/kin.20763>
  • Behrendt Philipp J., Kim Hee-Cheol, Hampp Norbert: Laser-based depletion zone photoreaction: Selective synthesis of [2+2]-crossdimers of coumarin and 5-fluorouracil. Journal of Photochemistry and Photobiology A: Chemistry 2013, 264, 67. <http://dx.doi.org/10.1016/j.jphotochem.2013.05.006>
  • Bos Pieter H., Antalek Mitchell T., Porco John A., Stephenson Corey R. J.: Tandem Dienone Photorearrangement–Cycloaddition for the Rapid Generation of Molecular Complexity. J. Am. Chem. Soc. 2013, 135, 17978. <http://dx.doi.org/10.1021/ja409992m>
  • Shi Zhengwei, Cui Yue-Zhi, Huang Su, Li Zhong’an, Luo Jingdong, Jen Alex K.-Y.: Dipolar Chromophore Facilitated Huisgen Cross-Linking Reactions for Highly Efficient and Thermally Stable Electrooptic Polymers. ACS Macro Lett. 2012, 1, 793. <http://dx.doi.org/10.1021/mz300189p>
  • Ponomarov Oleksandr, Laws Andrew P., Hanusek Jiří: 1,2,4-Dithiazole-5-ones and 5-thiones as efficient sulfurizing agents of phosphorus(iii) compounds – a kinetic comparative study. Org. Biomol. Chem. 2012, 10, 8868. <http://dx.doi.org/10.1039/c2ob26460a>
  • McGrath Nicholas A., Raines Ronald T.: Diazo compounds as highly tunable reactants in 1,3-dipolar cycloaddition reactions with cycloalkynes. Chem. Sci. 2012, 3, 3237. <http://dx.doi.org/10.1039/c2sc20806g>
  • Jasiński Radomir, Kwiatkowska Magdalena, Barański Andrzej: Stereoselectivity and kinetics of [4 + 2] cycloaddition reaction of cyclopentadiene to para-substituted E-2-arylnitroethenes. J Phys Org Chem 2011, n/a. <http://dx.doi.org/10.1002/poc.1853>
  • Benchouk W., Mekelleche S. M., Silvi B., Aurell M. J., Domingo L. R.: Understanding the kinetic solvent effects on the 1,3-dipolar cycloaddition of benzonitrile N-oxide: a DFT study. J Phys Org Chem 2011, 24, 611. <http://dx.doi.org/10.1002/poc.1858>
  • de Cózar Abel, Cossío Fernando P.: Stereocontrolled (3+2) cycloadditions between azomethine ylides and dipolarophiles: a fruitful interplay between theory and experiment. Phys Chem Chem Phys 2011, 13, 10858. <http://dx.doi.org/10.1039/c1cp20682f>
  • Derrah Eric J., Pantazis Dimitrios A., McDonald Robert, Rosenberg Lisa: Concerted [2+2] Cycloaddition of Alkenes to a Ruthenium-Phosphorus Double Bond. angew chemie 2010, 122, 3439. <http://dx.doi.org/10.1002/ange.201000356>
  • Derrah Eric J., Pantazis Dimitrios A., McDonald Robert, Rosenberg Lisa: Concerted [2+2] Cycloaddition of Alkenes to a Ruthenium-Phosphorus Double Bond. Angew Chem Int E 2010, 49, 3367. <http://dx.doi.org/10.1002/anie.201000356>
  • Meir Rinat, Chen Hui, Lai Wenzhen, Shaik Sason: Oriented Electric Fields Accelerate Diels–Alder Reactions and Control the endo/exo Selectivity. Chem Eur J of Chem Phys 2010, 11, 301. <http://dx.doi.org/10.1002/cphc.200900848>
  • Štefane Bogdan, Perdih Andrej, Pevec Andrej, Šolmajer Tomaž, Kočevar Marijan: The Participation of 2H-Pyran-2-ones in [4+2] Cycloadditions: An Experimental and Computational Study. Eur J Org Chem 2010, 2010, 5870. <http://dx.doi.org/10.1002/ejoc.201000236>
  • Scheeren J. W.: Synthetic and mechanistic aspects of thermal (2 + 2) cycloadditions of ketene acetals with electron-poor alkenes and carbonyl compounds. Recl Trav Chim Pays-Bas 2010, 105, 71. <http://dx.doi.org/10.1002/recl.19861050302>
  • Noack Rainer, Schwetlick Klaus: Cycloadditionen mit Isocyanaten - Reaktionsmöglichkeiten, Kinetik, Mechanismen. Z Chem 2010, 26, 117. <http://dx.doi.org/10.1002/zfch.19860260402>
  • Zhang Xing-hui, Geng Zhi-yuan: Reaction pathways of the [2+2] cycloaddition between formaldehyde with ketene and isocyanic acid: A theoretical investigation. Journal of Molecular Structure: THEOCHEM 2010, 955, 33. <http://dx.doi.org/10.1016/j.theochem.2010.05.024>
  • Iwata Shin, Hamura Toshiyuki, Suzuki Keisuke: Siloxy(trialkoxy)ethene undergoes regioselective [2+2] cycloaddition to ynones and ynoates en route to functionalized cyclobutenediones. Chem Commun 2010, 46, 5316. <http://dx.doi.org/10.1039/c0cc00883d>
  • Avenoza Alberto, Busto Jes?s H., Canal Noelia, Garc?a Jos? I., Jim?nez-Os?s Gonzalo, Peregrina Jes?s M., P?rez-Fern?ndez Marta: Mechanistic study of the ring-size modulation in Michael?Dieckmann type reactions of 2-acylaminoacrylates with ketene diethyl acetal. New J Chem 2007, 31, 224. <http://dx.doi.org/10.1039/b615220a>
  • Ess Daniel H., Jones Gavin O., Houk K. N.: Conceptual, Qualitative, and Quantitative Theories of 1,3-Dipolar and Diels–Alder Cycloadditions Used in Synthesis. Adv Synth Catal 2006, 348, 2337. <http://dx.doi.org/10.1002/adsc.200600431>
  • Tidwell Thomas T.: Ein Jahrhundert Ketene (1905-2005): die Entdeckung einer vielseitigen Klasse reaktiver Intermediate. Angew Chem 2005, 117, 5926. <http://dx.doi.org/10.1002/ange.200500098>
  • Tidwell Thomas T.: The First Century of Ketenes (1905-2005): The Birth of a Versatile Family of Reactive Intermediates. Angew Chem Int Ed 2005, 44, 5778. <http://dx.doi.org/10.1002/anie.200500098>
  • Okamoto Junko, Yamabe Shinichi, Minato Tsutomu, Hasegawa Toshio, Machiguchi Takahisa: Tropone Is a Mere Ketone for Cycloadditions to Ketenes. HCA 2005, 88, 1519. <http://dx.doi.org/10.1002/hlca.200590121>
  • Rispens Theo, Engberts Jan B. F. N.: Kinetic solvent effects on 1,3-dipolar cycloadditions of benzonitrile oxide. J Phys Org Chem 2005, 18, 908. <http://dx.doi.org/10.1002/poc.917>
  • Rispens Theo, Engberts Jan B. F. N.: Cycloadditions in mixed aqueous solvents: the role of the water concentration. J. Phys. Org. Chem. 2005, 18, 725. <http://dx.doi.org/10.1002/poc.926>
  • Fringuelli Francesco, Piermatti Oriana, Pizzo Ferdinando, Vaccaro Luigi: Recent Advances in Lewis Acid Catalyzed Diels−Alder Reactions in Aqueous Media. Eur J Org Chem 2001, 2001, 439. <http://dx.doi.org/10.1002/1099-0690(200102)2001:3<439::AID-EJOC439>3.0.CO;2-B>
  • Gholami M. R., Yangjeh A. Habibi: Multiparameter correlation of the rate of a [2 + 2] cycloaddition reaction versus solvophobicity parameter and normalized polarity parameter in aqueous solutions. J Phys Org Chem 2000, 13, 468. <http://dx.doi.org/10.1002/1099-1395(200008)13:8<468::AID-POC258>3.0.CO;2-E>
  • Desimoni Giovanni, Faita Giuseppe, Guidetti Sergio, Righetti Pier Paolo: The Electrocyclic Reactions. Eur J Org Chem 1999, 1999, 1921. <http://dx.doi.org/10.1002/(SICI)1099-0690(199908)1999:8<1921::AID-EJOC1921>3.0.CO;2-N>
  • Kuo Cheng-Yi, Fuh Yaw-Shyan, Chaen Ming-Cheng, Yu Shuchun Joyce: Homogeneous Diels-Alder catalysis by organotungsten Lewis acid containing tris(2-pyridyl)phosphine ligand. Tetrahetron Lett 1999, 40, 6451. <http://dx.doi.org/10.1016/S0040-4039(99)01284-8>
  • Apostoluk Wiesław, Szymanowski Jan: Application of the Kamlet and Taft model in solvent extraction chemistry of metals. Analytica Chimica Acta 1998, 374, 137. <http://dx.doi.org/10.1016/S0003-2670(98)00468-1>
  • Loomis Richard A., Leone Stephen R., Gilles Mary K.: Novel five-membered ring intermediates in gas phase reactions. Res. Chem. Intermed. 1998, 24, 707. <http://dx.doi.org/10.1163/156856798X00384>
  • Wijnen Jan W., Engberts Jan B. F. N.: A Hetero Retro Diels–Alder Reaction in Aqueous Solution: A Dramatic Water-Induced Increase of the Equilibrium Constant and Inhibition of Cycloreversion. Liebigs Ann /Recueil 1997, 1997, 1085. <http://dx.doi.org/10.1002/jlac.199719970607>
  • Sauer Jürgen, Schuhbauer Hans Markus: Solvent Effects in [4+2] Cycloadditions of Polyhalogenated Cyclopentadienes with 4-Phenyl-1,2,4-triazoline-3,5-dione. Liebigs Ann /Recueil 1997, 1997, 1739. <http://dx.doi.org/10.1002/jlac.199719970816>
  • Desimoni Giovanni, Faita Giuseppe, Garau Stefano, Righetti PierPaolo: Solvent effect in pericyclic reactions. X. The cheletropic reaction. Tetrahedron 1996, 52, 6241. <http://dx.doi.org/10.1016/0040-4020(96)00279-7>
  • Fallahpour Reza-Ali, Hansen Hans-Jürgen: Formation and Thermal Rearrangement of Dimethyl Tricyclo[6.2.2.01,7]dodeca-2,4,6,9,11-pentaene-9,10-dicarboxylates. HCA 1995, 78, 1933. <http://dx.doi.org/10.1002/hlca.19950780805>
  • Wijnen Jan W., Steiner Roberto A., Engberts Jan B.F.N.: 1,3-dipolar cycloaddition of phenyl azide to norbornene in aqueous solutions. Tetrahetron Lett 1995, 36, 5389. <http://dx.doi.org/10.1016/0040-4039(95)00987-N>
  • Bernardi Fernando, Pappalardo Rafael R., Robb Michael A., Venturini Alessandro, Wilson S., Morley John O.: An ab initio MC-SCF study of the solvent effects in polar and non-polar [2 + 2] cycloadditions. Journal of Molecular Structure: THEOCHEM 1995, 357, 33. <http://dx.doi.org/10.1016/0166-1280(95)04276-C>
  • Desimoni G., Faita G., Righetti P.P., Sfulcini A., Tsyganov D.: Solvent effect in pericyclic reactions. IX. The ene reaction. Tetrahedron 1994, 50, 1821. <http://dx.doi.org/10.1016/S0040-4020(01)80854-1>
  • Burdisso Marina, Gandolfi Remo, Toma Lucio, Oberti Roberta: Hexafluoroisopropanol as a suitable solvent for rearrangements via zwitterionic intermediates. Tetrahedron 1991, 47, 6725. <http://dx.doi.org/10.1016/S0040-4020(01)82324-3>
  • Bochler Mark A., Konopelski Joseph P.: Enantiomerically pure vinylketene acetals in the Diels-Alder reaction. Catalysis and facial selectivity. Tetrahedron 1991, 47, 4519. <http://dx.doi.org/10.1016/S0040-4020(01)86459-0>
  • Desimoni G., Faita G., Righetti P.P.: Solvent effect as the result of frontier molecular orbital interaction. VI. The Diels-Alder reactions of an N-acyl-o-quinone monoimide behaving as diene or dienophile. Tetrahedron 1991, 47, 5857. <http://dx.doi.org/10.1016/S0040-4020(01)86536-4>
  • Al-Husaini Abdulrahman H., Muqtar Mohammed, Ali Sk.Asrof: Study of ketene-alkene cycloadditions and cycloreversions of cyclobutanones. Tetrahedron 1991, 47, 7719. <http://dx.doi.org/10.1016/S0040-4020(01)88296-X>
  • Kim Eunkyoung, Kochi Jay K., Christl Manfred: Charge-Transfer Cycloaddition of Homobenzvalene with Tetracyanoethylene. Chem Ber 1990, 123, 1209. <http://dx.doi.org/10.1002/cber.19901230538>
  • Majchrzak Michael W., Warkentin John: Cycloadditions of 2-diazopropane to bicyclo[2.2.1]hept-2-enes. Direct experimental evidence for an asynchronous mechanism. J Phys Org Chem 1990, 3, 339. <http://dx.doi.org/10.1002/poc.610030511>
  • Brückner Reinhard, Huisgen Rolf: Kinetics of [2+2] cycloadditions of 2,2-bis(trifluoromethylethylene-1,1-dicarbonitrile with enol ethers, 1,1-dimethylbutadiene, and allyltrimethylsilane. Tetrahetron Lett 1990, 31, 2557. <http://dx.doi.org/10.1016/0040-4039(90)80124-5>
  • Kochi Jay K.: Elektronen- und Ladungsübertragung: Zur Vereinheitlichung der Mechanismen organischer und metallorganischer Reaktionen. Angew Chem 1988, 100, 1331. <http://dx.doi.org/10.1002/ange.19881001008>
  • Dannhardt Gerd, Grobe Andrea, Obergrusberger Richard: 4H-Thiopyrane und 4H-Thiocine mit spiroanelliertem Pyrrolidinring. Arch Pharm Pharm Med Chem 1987, 320, 455. <http://dx.doi.org/10.1002/ardp.19873200514>
  • Fobbe Helmut, Neumann Wilhelm P.: Organozinnverbindungen. J Organomet Chem 1986, 303, 87. <http://dx.doi.org/10.1016/0022-328X(86)80114-0>
  • Corsaro Antonino, Chiacchio Ugo, Perrini Giancarlo, Caramella Pierluigi, Purrello Giovanni: The site-selectivity of cycloadditions of nitrile oxides to β-aminocinnamonitriles. A remarkable solvent dependence. J Heterocyclic Chem 1985, 22, 797. <http://dx.doi.org/10.1002/jhet.5570220336>
  • Corsaro Antonino, Chiacchio Ugo, Caramella Pierluigi, Purrello Giovanni: Activation of nitriles by hydrogen bonding in cycloadditions with nitrile oxides. J Heterocyclic Chem 1984, 21, 949. <http://dx.doi.org/10.1002/jhet.5570210403>
  • Corsico Coda A., Desimoni G., Ferrari E., Righetti P.P., Tacconi G.: Solvent effect as the result of frontier molecular orbital interaction-1. Tetrahedron 1984, 40, 1611. <http://dx.doi.org/10.1016/S0040-4020(01)91813-7>
  • Reichardt Christian, Harbusch-Görnert Erwin: Über Pyridinium-N-phenolat-Betaine und ihre Verwendung zur Charakterisierung der Polarität von Lösungsmitteln, X. Erweiterung, Korrektur und Neudefinition derET-Lösungsmittelpolaritätsskala mit Hilfe eines lipophilen penta-tert-butyl-substituierten Pyridinium-N-phenolat-Betainfarbstoffes. Liebigs Ann Chem 1983, 1983, 721. <http://dx.doi.org/10.1002/jlac.198319830502>
  • Scheeren Hans W., Vas Rossum Anton J.R., Nivard Rutger J.F.: The influence of the Π-electron distribution and Π -bond stability of ketene acetals on their reactivity and stereoselectivity in thermal (2 + 2) cycloadditions with 1,1-dicyanostyrenes. Tetrahedron 1983, 39, 1345. <http://dx.doi.org/10.1016/S0040-4020(01)91903-9>
  • Fukuzumi S., Kochi J.K.: Electron transfer activation of the Diels-Alder reaction. Tetrahedron 1982, 38, 1035. <http://dx.doi.org/10.1016/0040-4020(82)80121-X>