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Pure Appl. Chem., 1981, Vol. 53, No. 1, pp. 171-187

Recent contributions to the mechanism of concerted and non-concerted cycloadditions

R. Huisgen

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  • Wang Hao, Houk K. N.: Torsional control of stereoselectivities in electrophilic additions and cycloadditions to alkenes. Chem. Sci. 2014, 5, 462. <>
  • Louhichi Nesrine, Houas Amel, Hamadi Naoufel Ben, Msaddek Moncef: Synthesis and chemistry of new spiro-Δ1-pyrazoline. J  Heterocycl Chem 2012, 49, 267. <>
  • Steinmann Stephan N., Vogel Pierre, Mo Yirong, Corminboeuf Clémence: The norbornene mystery revealed. Chem Commun 2011, 47, 227. <>
  • Schmitt Gérard, Laude Bernard, Vebrel Joël, Rodier Noël, Theobald François: Reaction du fluoroborate du benzoyl-2 dihydro-1,2 isoquinaldonitrile avec les esters α,β-ethyleniques cas des esters acrylique, fumarique et maleique. Competition entre les reactions de cycloaddition [3+2] et [4+2]. Bull Soc Chim Belges 2010, 98, 113. <>
  • Vogel Pierre: Synthesis of Rare Carbohydrates and Biomolecules from Furan. Bull Soc Chim Belges 2010, 99, 395. <>
  • Bakker C. G., Ooms P. H. M., Scheeren J. W., Nivard R. J. F.: Chemistry of ketene acetals VI. The influence of the dicyanoethene moiety on the reactivity and selectivity of β,β-dicyano-α,β-unsaturated ketones in cycloadditions with ketene acetals. Recl Trav Chim Pays-Bas 2010, 102, 130. <>
  • Braida Benoit, Walter Christof, Engels Bernd, Hiberty Philippe C.: A Clear Correlation between the Diradical Character of 1,3-Dipoles and Their Reactivity toward Ethylene or Acetylene. J Am Chem Soc 2010, 132, 7631. <>
  • Schoenebeck Franziska, Ess Daniel H., Jones Gavin O., Houk K. N.: Reactivity and Regioselectivity in 1,3-Dipolar Cycloadditions of Azides to Strained Alkynes and Alkenes: A Computational Study. J Am Chem Soc 2009, 131, 8121. <>
  • Chakrabarty Kuheli, Roy Sukhendu, Das Gourab Kanti, Mondal Nityagopal: Pi-diastereofacial selectivity on carbonyl enophile in carbonyl ene reaction: A new insight on the substituent effect in ene cyclization. Journal of Molecular Structure: THEOCHEM 2007, 805, 1. <>
  • Mawhinney Robert C, Muchall Heidi M, Peslherbe Gilles H: A computational study of the 1,3-dipolar cycloaddition reaction mechanism for nitrilimines. Can J Chem 2005, 83, 1615. <>
  • Nguyen Loc Thanh, Proft Frank De, Dao Van Luong, Nguyen Minh Tho, Geerlings Paul: A theoretical approach to the regioselectivity in 1,3-dipolar cycloadditions of diazoalkanes, hydrazoic acid and nitrous oxide to acetylenes, phosphaalkynes and cyanides. J Phys Org Chem 2003, 16, 615. <>
  • Kuznetsov Maxim L., Kukushkin Vadim Yu., Haukka Matti, Pombeiro Armando J.L.: 1,3-Dipolar cycloaddition of nitrile oxides to free and Pt-bound nitriles: a theoretical study of the activation effect, reactivity and mechanism. Inorg Chim Ada 2003, 356, 85. <>
  • Martı́nez Rafael, Jiménez-Vázquez Hugo A, Delgado Francisco, Tamariz Joaquı́n: Synthesis and highly selective Diels–Alder cycloadditions of the new dienes N-substituted 2,3,5,6-tetrahydrobenzoxazol-2-ones. Tetrahedron 2003, 59, 481. <>
  • Hanessian Stephen, Bayrakdarian Malken: Asymmetric synthesis of diversely substituted N-hydroxypyrrolidines using cycloadditions with chiral nitrone enolate/ylids. Tetrahetron Lett 2002, 43, 967. <>
  • Böhm Thomas, Weber Andreas, Sauer Jürgen: Nonstereospecific 1,3-dipolar cycloadditions of azomethine ylides and enamines. Tetrahedron 1999, 55, 9535. <>
  • Benkhoff Johannes, Boese Roland, Klärner Frank-Gerrit: Synthesis of Sterically Rigid Macrocycles by The Use of Pressure-Induced Repetitive Diels–Alder Reactions. Liebigs Ann /Recueil 1997, 1997, 501. <>
  • Weinrich Volker, Geisbauer Andreas, Sünkel Karlheinz, Beck Wolfgang: Hydrocarbon bridged metal complexes. XXXIV. Synthesis, structure and attempted decarbonylation of a trans 11,12-bis(dicarbonylcyclopentadienylironacyl) substituted dihydro 9,10-ethanoanthracene. J Organomet Chem 1996, 515, 173. <>
  • Bialecki Maciej, Vogel Pierre: Stereoselective Synthesis of 2,4,6-Trimethylcyclohex-4-ene-1,3-diol Derivatives and of polypropionate fragments with four contiguous stereogenic centers. HCA 1995, 78, 325. <>
  • Fallahpour Reza-Ali, Hansen Hans-Jürgen: Formation and Thermal Rearrangement of Dimethyl Tricyclo[,7]dodeca-2,4,6,9,11-pentaene-9,10-dicarboxylates. HCA 1995, 78, 1933. <>
  • Fröhlich J., Fišera L., Sauter F., Feng Y., Ertl P.: Regioselectivity of cycloadditions of nitrile oxides and nitrones to 4-methylene-tetrahydrothiopyrane. Monatsh Chem 1995, 126, 75. <>
  • Toyota Akemi, Aizawa Megumi, Habutani Chie, Katagiri Nobuya, Kaneko Chikara: Addition of molecular fluorine to 2-azabicyclo[2.2.1]hept-5-en-3-one and related compounds: Synthesis of difluorinated carbocyclic nucleosides. Tetrahedron 1995, 51, 8783. <>
  • Jaroškoá L., Fišera L'., Matejková I., Ertl P., Prónayová N.: Stereoselectivity in the 1,3-dipolar cycloaddition of nitrones to 1-substituted 3,3-methylene-5,5-dimethyl-2-pyrrolidinones. Monatsh Chem 1994, 125, 1413. <>
  • Fišera L., Sauter F., Fröhlich J., Feng Y., Ertl P., Mereiter K.: Cycloadditions of nitrile oxides and nitrones to 4,4-methylene-1-methylpiperidine: Studies in regio- and stereoselectivity. Monatsh Chem 1994, 125, 553. <>
  • Toyota Akemi, Habutani Chie, Katagiri Nobuya, Kaneko Chikara: Addition of molecular fluorine to bicyclo[2.2.1]hept-2-ene derivatives and conversion to fluorine-containing carbocyclic nucleosides. Tetrahetron Lett 1994, 35, 5665. <>
  • Irngartinger Hermann, Oeser Thomas, Jahn Reiner, Kallfaß Dietmar: Pyramidalization of the sp2-Hybridized Carbon Atoms in 1,4-Bridged 2,5-Cyclohexadienes. Chem Ber 1992, 125, 2067. <>
  • Rzepa Henry S., Wylie William A.: Transition-state structures for the reaction between styrene andtbutyl cyanoketene: Theoretical evidence for antarafacial characteristics in a π2 + π2 thermal cycloaddition. Int J Quantum Chem 1992, 44, 469. <>
  • Brandi Alberto, Cordero Franca M., Sarlo Francesco De, Gandolfi Remo, Rastelli Andrea, Bagatti Marisa: The regioselectivity of nitrone and nitrile oxide cycloadditions to alkylidenecyclopropanes. Tetrahedron 1992, 48, 3323. <>
  • Stájer Géza, Frimpong-Manso Samuel, Bernáth Gábor, Sohár Pál: Preparation of diastereomeric 5,8-methanobenzoxazino[2,1-6]- and [2,3-6]-1,3-benzoxazin-4-ones by reaction of norbornane/ene-condensed dihydro-1,3-oxazines with salicyl chloride. J Heterocyclic Chem 1991, 28, 753. <>
  • Sohár Pál, Stájer Géza, Szabó Angela E., Bernáth Gábor: NMR/NOE elucidation of the stereostructure of cycloadducts of acetonitrile oxide with norbornane/ene-fused dihydro-oxazines. Magn Reson Chem 1991, 29, 706. <>
  • Burdisso Marina, Gandolfi Remo: Diastereofacial selectivity in 1,3-dipolar cycloadditions. Reactions of diazomethane with endo,cis-5,6-disubstituted bicyclo[2.2.2]oct-2-enes. Tetrahedron 1991, 47, 7699. <>
  • Aurich Hans Günter, Boutahar Mostafa, Köster Heiner, Möbus Klaus-Dieter, Ruiz Luis: Intramolekulare Cycloaddition von Nitronen. Chem Ber 1990, 123, 1999. <>
  • 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. <>
  • Carrupt Pierre-Alain, Vogel Pierre: The Carbonyl Group as Homoconjugated Electron-Releasing Substituent. Regioselective electrophilic additions at bicyclo[2.2.1]hept-5-en-2-one, bicyclo[2.2.2]oct-5-en-2-one, and derivatives. HCA 1989, 72, 1008. <>
  • Gössinger Edda, Müller Renate: A versatile regio- and stereospecific annulation method - I. Tetrahedron 1989, 45, 1377. <>
  • Kochi Jay K.: Elektronen- und Ladungsübertragung: Zur Vereinheitlichung der Mechanismen organischer und metallorganischer Reaktionen. Angew Chem 1988, 100, 1331. <>
  • Hertkorn N., Köhler F.H.: Selektive Metallierung von Bicyclo[3.2.1]octa-2,6-dien. J Organomet Chem 1988, 355, 19. <>
  • Burdisso Marina, Gamba Anna, Gandolfi Remo, Oberti Roberta: Steric effects vs secondary orbital interactions in nitrone cycloadditions. Tetrahedron 1988, 44, 3735. <>
  • Dannhardt Gerd, Grobe Andrea, Obergrusberger Richard: 4H-Thiopyrane und 4H-Thiocine mit spiroanelliertem Pyrrolidinring. Arch Pharm Pharm Med Chem 1987, 320, 455. <>
  • Schaumann Ernst, Dietz Jörg, Kausch Erwin, Schmerse Gerd C.: Alkyl Shifts in 1,4-Dipoles from Tosyl Iso(thio)cyanate and Imido(thio)carbonates or Isoureas. Chem Ber 1987, 120, 339. <>
  • Claret François, Carrupt Pierre-Alain, Vogel Pierre: Regioselective Electrophilic Additions of Bicyclo[2.2.n]alk-2-enes Controlled by Remote Epoxide Functions. HCA 1987, 70, 1886. <>
  • Wiberg Nils, Kim Chung-Kyun: Reaktivität des Germaethens Me2GeC(SiMe3)2. Chem Ber 1986, 119, 2980. <>
  • Pradhan Suresh K.: Mechanism and stereochemistry of alkali metal reductions of cyclic saturated and unsaturated ketones in protic solvents. Tetrahedron 1986, 42, 6351. <>
  • Eberbach Wolfgang, Trostmann Uwe: Butadienyloxiran-Dihydrooxepin-Isomerisierung. Ringerweiterungsreaktionen von sterisch fixierten und benzoanellierten Epoxyhexadienen durch 1,7-Elektrocyclisierung konjugierter Carbonyl-Ylide. Chem Ber 1985, 118, 4035. <>
  • Carrupt Pierre-Alain, Vogel Pierre, Meyer A.Y.: Double bond pyramidalization in bicyclic alkanes. Ab initio mo calculations on bicyclo[2.2.1] hept-2-ene, bicyclo[2.2.1] hex-2-ene and bicyclo[3.2.1] oct-6-ene derivatives. Journal of Molecular Structure: THEOCHEM 1985, 124, 9. <>
  • Alonso Miguel E., Hernández Maria I., Gómez Matilde, Jano Patricia, Pekerar Sarah: On the question of free radical intermediacy in cycloaddition reactions of diazocarbonyl compounds to olefins under copper(II) chelate catalysis. Tetrahedron 1985, 41, 2347. <>
  • Brokatzky-Geiger Jürgen, Eberbach Wolfgang: Intramolekulare Cycloadditionen mit Carbonyl-Yliden: Von Oxiranen zu großen Ringen. Chem Ber 1984, 117, 2157. <>
  • Pinkerton A. Alan, Schwarzenbach Dieter, Birbaum Jean-Luc, Carrupt Pierre-Alain, Schwager Luis, Vogel Pierre: The Non-planarity of the Bicyclo[2.2.1]hept-2-ene Double bond. Crystal Structures of Bicyclo[2.2.2]oct-2-ene, Bicyclo[2.2.1]hept-2-ene, and Bicyclo[2.1.1]hex-2-ene Systems. HCA 1984, 67, 1136. <>
  • Avenati Macro, Vogel Pierre: Face Selectivity of theDiels-Alder Reaction of 5,6-Bis((D)methylidene)-2-bicyclo[2.2.2]octene. HCA 1983, 66, 1279. <>
  • Spanget-Larsen Jens, Gleiter Rolf: Structure and reactivity of norbornene and syn-sesquinorbornene. Tetrahedron 1983, 39, 3345. <>
  • Flemming S.: On the molecular and electronic features of syn- and anti-sequinorbornene. Tetrahetron Lett 1983, 24, 5289. <>
  • Adam Waldemar, Beinhauer Axel, De Lucchi Ottorino, Rosenthal Robert J.: Dienophilic and dipolar additions to bicyclo[2.1.0]pent-2-ene. Tetrahetron Lett 1983, 24, 5727. <>
  • Erden Ihsan, de Meijere Armin: Stereoselectivities of dichloroketene cycloadditions to bridged bicyclic olefins. Tetrahetron Lett 1983, 24, 3811. <>
  • Avenati Marco, Vogel Pierre: Face Selectivity of theDiels-Alder Additions of 2-Substituted 5,6-bis((E)-chloromethylidene)bicyclo[2.2.2]octanes. HCA 1982, 65, 204. <>
  • Fukuzumi S., Kochi J.K.: Electron transfer activation of the Diels-Alder reaction. Tetrahedron 1982, 38, 1035. <>
  • Lluch J.M., Bertrán J.: Theoretical interpretation of experimental data on 1,3-dipolar cycloadditions. Tetrahedron 1982, 38, 1847. <>
  • Sanhueza J.E., Tapia O., Sana M., Leroy G., Dive G., Nguyen M.T., Aleksanyan V.T., Antipov B.G.: The quantum chemical calculation of environmental effects: A comparative study of charge separation in water dimers. Journal of Molecular Structure: THEOCHEM 1982, 89, 131. <>
  • Gleiter Rolf, Spanget-Larsen Jens: On the ground state and first excited state geometries of syn-sesquinorbornene. Tetrahetron Lett 1982, 23, 927. <>
  • Spanget-Larsen Jens, Gleiter Rolf: On the exceptional reactivity of the norbornene double bond. Tetrahetron Lett 1982, 23, 2435. <>
  • Carrupt Pierre-Alain, Vogel Pierre: Regioselective additions of electrophiles to olefins remotely perturbed. The carbonyl group as a homoconjugated electron donating substituent. Tetrahetron Lett 1982, 23, 2563. <>
  • Hagenbuch Jean-Pierre, Vogel Pierre, Pinkerton A. Alan, Schwarzenbach Dieter: The π-Anisotropy of the Double Bond of asyn-11-Oxasesquinorbornene Derivative.. Stereoselectivity of theDiels-Alder additions of (2-norborneno)[c]furan. Crystal structure of 11-oxa-endo-tetracyclo[,6.02,7]-dodec-2(7)-ene-9,10-exo-dicarboxylic anhydride. HCA 1981, 64, 1818. <>