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Volumn 2, Issue 1, 2010, Pages 76-97

Recent studies on the aromaticity and antiaromaticity of planar cyclooctatetraene

Author keywords

Antiaromaticity; Cyclooctatetraene; NMR chemical shifts; Quantum chemical calculations; Ring current

Indexed keywords


EID: 77956167349     PISSN: None     EISSN: 20738994     Source Type: Journal    
DOI: 10.3390/sym2010076     Document Type: Review
Times cited : (94)

References (96)
  • 1
    • 84981750751 scopus 로고
    • Über Cyclo-octatetraen
    • Willstätter, R.; Waser, E. Über Cyclo-octatetraen. Chem. Ber 1911, 44, 3423-3445.
    • (1911) Chem. Ber , vol.44 , pp. 3423-3445
    • Willstätter, R.1    Waser, E.2
  • 2
    • 84979186465 scopus 로고
    • Zur Kenntnis des Cyclo-octatetraens
    • Willstätter, R.; Heidelberger, M. Zur Kenntnis des Cyclo-octatetraens. Chem Ber. 1913, 46, 517-527.
    • (1913) Chem Ber , vol.46 , pp. 517-527
    • Willstätter, R.1    Heidelberger, M.2
  • 3
    • 0002587427 scopus 로고
    • An Electron Diffraction Investigation of Cyclooctatetraene and Benzene
    • Karle, I.L. An Electron Diffraction Investigation of Cyclooctatetraene and Benzene. J. Chem. Phys. 1952, 20, 65-70.
    • (1952) J. Chem. Phys. , vol.20 , pp. 65-70
    • Karle, I.L.1
  • 4
    • 0000784475 scopus 로고
    • Reinvestigation of the Molecular Structure of 1,3,5,7-Cyclooctatetraene by Electron Diffraction
    • Bastiansen, O.; Hedberg, L.; Hedberg, K. Reinvestigation of the Molecular Structure of 1,3,5,7-Cyclooctatetraene by Electron Diffraction. J. Chem. Phys. 1957, 27, 1311-1317.
    • (1957) J. Chem. Phys. , vol.27 , pp. 1311-1317
    • Bastiansen, O.1    Hedberg, L.2    Hedberg, K.3
  • 5
    • 0001262412 scopus 로고
    • The Molecular Structure of 1,3,5,7-Cyclo-octatetraene
    • Traetteberg, M. The Molecular Structure of 1,3,5,7-Cyclo-octatetraene. Acta Chem. Scand. 1966, 20, 1724-1726.
    • (1966) Acta Chem. Scand. , vol.20 , pp. 1724-1726
    • Traetteberg, M.1
  • 7
    • 0010762104 scopus 로고
    • Quantentheoretische Beiträge zum Benzolproblem
    • Hückel, E. Quantentheoretische Beiträge zum Benzolproblem. Z. Phys. 1931, 70, 204-286.
    • (1931) Z. Phys. , vol.70 , pp. 204-286
    • Hückel, E.1
  • 8
    • 33750188916 scopus 로고    scopus 로고
    • Cyclobutadiene: The Antiaromatic Paradigm? Angew
    • Bally, T. Cyclobutadiene: The Antiaromatic Paradigm? Angew. Chem. Int. Ed. 2006, 45, 6616-6619.
    • (2006) Chem. Int. Ed. , vol.45 , pp. 6616-6619
    • Bally, T.1
  • 9
    • 0035353482 scopus 로고    scopus 로고
    • Antiaromaticity in Monocyclic Conjugated Carbon Rings
    • Wiberg, K.B. Antiaromaticity in Monocyclic Conjugated Carbon Rings. Chem. Rev. 2001, 101, 1317-1331.
    • (2001) Chem. Rev. , vol.101 , pp. 1317-1331
    • Wiberg, K.B.1
  • 10
    • 0035353519 scopus 로고    scopus 로고
    • Antiaromaticity in Open-Shell Cyclopropenyl to Cycloheptatrienyl Cations, Anions, Free Radicals, and Radical Ions
    • Allen, A.D.; Tidwell, T.T. Antiaromaticity in Open-Shell Cyclopropenyl to Cycloheptatrienyl Cations, Anions, Free Radicals, and Radical Ions. Chem. Rev. 2001, 101, 1333-1348.
    • (2001) Chem. Rev. , vol.101 , pp. 1333-1348
    • Allen, A.D.1    Tidwell, T.T.2
  • 12
    • 0001637883 scopus 로고
    • Antiaromaticity
    • Breslow, R. Antiaromaticity. Acc. Chem. Res. 1973, 6, 393-398.
    • (1973) Acc. Chem. Res. , vol.6 , pp. 393-398
    • Breslow, R.1
  • 14
    • 0001683740 scopus 로고
    • CASSCF Calculations Find that a D8h Geometry is the Transition State for Double Bond Shifting in Cyclooctatetraene
    • Hrovat, D.A.; Borden, W.T. CASSCF Calculations Find that a D8h Geometry is the Transition State for Double Bond Shifting in Cyclooctatetraene. J. Am. Chem. Soc. 1992, 114, 5879-5881.
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 5879-5881
    • Hrovat, D.A.1    Borden, W.T.2
  • 15
    • 0009928506 scopus 로고
    • Effects of electron repulsion in conjugated hydrocarbon diradicals
    • Borden, W.T.; Davidson, E.R. Effects of electron repulsion in conjugated hydrocarbon diradicals. J. Am. Chem. Soc. 1977, 99, 4587-4594.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 4587-4594
    • Borden, W.T.1    Davidson, E.R.2
  • 16
    • 0001142932 scopus 로고
    • Violations of Hund's Rule in Non-Kekule Hydrocarbons: Theoretical Prediction and Experimental Verification
    • Borden, W.T.; Iwamura, H.; Berson, J.A. Violations of Hund's Rule in Non-Kekule Hydrocarbons: Theoretical Prediction and Experimental Verification. Acc. Chem. Res. 1994, 27, 109-116.
    • (1994) Acc. Chem. Res. , vol.27 , pp. 109-116
    • Borden, W.T.1    Iwamura, H.2    Berson, J.A.3
  • 18
    • 0000163113 scopus 로고
    • Planarization of Unsaturated Rings. Cycloheptatriene with a Planar Seven-Membered Ring
    • Ermer, O.; Klärner, F.-G.; Wette, M. Planarization of Unsaturated Rings. Cycloheptatriene with a Planar Seven-Membered Ring. J. Am. Chem. Soc. 1986, 108, 4908-4911.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 4908-4911
    • Ermer, O.1    Klärner, F.-G.2    Wette, M.3
  • 19
    • 0025317510 scopus 로고
    • Synthesis and Dynamic Behavior of (1,5)Cyclooctatetraenophanes. Effect of Distal Atom Bridging on Racemization Rates and Electrochemical Reducibility
    • Paquette, L. A.; Trova, M. P.; Luo, J.; Clough, A. E.; Anderson, L. B. Synthesis and Dynamic Behavior of (1,5)Cyclooctatetraenophanes. Effect of Distal Atom Bridging on Racemization Rates and Electrochemical Reducibility. J. Am. Chem. Soc. 1990, 112, 228-239.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 228-239
    • Paquette, L.A.1    Trova, M.P.2    Luo, J.3    Clough, A.E.4    Anderson, L.B.5
  • 20
    • 0025332408 scopus 로고
    • Is Pseudorotation the Operational Pathway for Bond Shifting within [8]Annulenes? Probe of Planarization Requirements by 1, 3-Annulation of the Cyclooctatetraene Ring. Kinetic Analysis of Racemization and 2-D NMR Quantitation of π-Bond Alternation and Ring Inversion as a Function of Polymethylene Chain Length
    • Paquette, L.A.; Wang, T.-Z.; Luo, J.; Cottrell, C.E.; Clough, A.E.; Anderson, L.B. Is Pseudorotation the Operational Pathway for Bond Shifting within [8]Annulenes? Probe of Planarization Requirements by 1,3-Annulation of the Cyclooctatetraene Ring. Kinetic Analysis of Racemization and 2-D NMR Quantitation of π-Bond Alternation and Ring Inversion as a Function of Polymethylene Chain Length. J. Am. Chem. Soc. 1990, 112, 239-253.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 239-253
    • Paquette, L.A.1    Wang, T.-Z.2    Luo, J.3    Cottrell, C.E.4    Clough, A.E.5    Anderson, L.B.6
  • 21
    • 12044257767 scopus 로고
    • The Current View of Dynamic Change within Cyclooctatetraenes
    • Paquette, L.A. The Current View of Dynamic Change within Cyclooctatetraenes. Acc. Chem. Res. 1993, 26, 57-62.
    • (1993) Acc. Chem. Res. , vol.26 , pp. 57-62
    • Paquette, L.A.1
  • 22
    • 33947487883 scopus 로고
    • Ring Inversion and Bond Shift in Cyclooctatetraene Derivatives
    • Anet, F.A.L.; Bourn, A.J.R.; Lin, Y.S. Ring Inversion and Bond Shift in Cyclooctatetraene Derivatives. J. Am. Chem. Soc. 1964, 86, 3576-3577.
    • (1964) J. Am. Chem. Soc. , vol.86 , pp. 3576-3577
    • Anet, F.A.L.1    Bourn, A.J.R.2    Lin, Y.S.3
  • 23
    • 84943700126 scopus 로고
    • Conformational Mobility and Fast Bond Shift in the Annulenes
    • Oth, J.F.M. Conformational Mobility and Fast Bond Shift in the Annulenes. Pure Appl. Chem. 1971, 25, 573-622.
    • (1971) Pure Appl. Chem. , vol.25 , pp. 573-622
    • Oth, J.F.M.1
  • 24
    • 0030921177 scopus 로고    scopus 로고
    • Experimental and Computational Studies of the Structures and Energetics of Cyclooctatetraene and Its Derivatives
    • Kato, S.; Lee, H.S.; Gareyev, R.; Wenthold, P.G.; Lineberger, W.C.; DePuy, C.H.; Bierbaum, V.M. Experimental and Computational Studies of the Structures and Energetics of Cyclooctatetraene and Its Derivatives. J. Am. Chem. Soc. 1997, 119, 7863-7864.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 7863-7864
    • Kato, S.1    Lee, H.S.2    Gareyev, R.3    Wenthold, P.G.4    Lineberger, W.C.5    DePuy, C.H.6    Bierbaum, V.M.7
  • 26
    • 0000434679 scopus 로고
    • The Rate of Bond Change in Cycloöctatetraene
    • Anet, F.A.L. The Rate of Bond Change in Cycloöctatetraene. J. Am. Chem. Soc. 1962, 84, 671-672.
    • (1962) J. Am. Chem. Soc. , vol.84 , pp. 671-672
    • Anet, F.A.L.1
  • 27
    • 84961474198 scopus 로고
    • Ring Inversion and Bond Shifting Energetics in Substituted Chiral Cyclooctatetraenes
    • Paquette, L.A.; Ring Inversion and Bond Shifting Energetics in Substituted Chiral Cyclooctatetraenes. Pure Appl. Chem. 1982, 54, 987-1004.
    • (1982) Pure Appl. Chem. , vol.54 , pp. 987-1004
    • Paquette, L.A.1
  • 28
    • 0025952513 scopus 로고
    • Synthesis, Structure, and Reduction of the Cyclooctatetraene Tetra-annelated with Bicyclo[2.2.2]-octene Frameworks
    • Komatsu, K.; Nishinaga, T.; Aonuma, S.; Hirosawa, C.; Takeuchi, K.; Lindner, H.J.; Richter, J. Synthesis, Structure, and Reduction of the Cyclooctatetraene Tetra-annelated with Bicyclo[2.2.2]-octene Frameworks. Tetrahedron Lett. 1991, 32, 6767-6770.
    • (1991) Tetrahedron Lett , vol.32 , pp. 6767-6770
    • Komatsu, K.1    Nishinaga, T.2    Aonuma, S.3    Hirosawa, C.4    Takeuchi, K.5    Lindner, H.J.6    Richter, J.7
  • 29
    • 84987059611 scopus 로고
    • Antiaromaticity in Relation to 1,3,5,7-Cyclooctatetraene Structures
    • Politzer, P.; Murray, J.S.; Seminario, J.M. Antiaromaticity in Relation to 1,3,5,7-Cyclooctatetraene Structures. Int. J. Quantum Chem. 1994, 50, 273-277.
    • (1994) Int. J. Quantum Chem. , vol.50 , pp. 273-277
    • Politzer, P.1    Murray, J.S.2    Seminario, J.M.3
  • 30
    • 0001645520 scopus 로고    scopus 로고
    • Isodesmic and homodesmotic stabilization energies of [n]annulenes and their relevance to aromaticity and antiaromaticity: is absolute antiaromaticity possible? J
    • Glukhovtsev, M.N.; Bach, R.D.; Laiter, S. Isodesmic and homodesmotic stabilization energies of [n]annulenes and their relevance to aromaticity and antiaromaticity: is absolute antiaromaticity possible? J. Mol. Struct. THEOCHEM 1997, 417, 123-129.
    • (1997) Mol. Struct. THEOCHEM , vol.417 , pp. 123-129
    • Glukhovtsev, M.N.1    Bach, R.D.2    Laiter, S.3
  • 31
    • 27744463786 scopus 로고    scopus 로고
    • Anisotropy of the Induced Current Density (ACID), a General Method To Quantify and Visualize Electronic Delocalization
    • Geuenich, D.; Hess, K.; Köhler, F.; Herges, R. Anisotropy of the Induced Current Density (ACID), a General Method To Quantify and Visualize Electronic Delocalization. Chem. Rev. 2005, 105, 3758-3772.
    • (2005) Chem. Rev. , vol.105 , pp. 3758-3772
    • Geuenich, D.1    Hess, K.2    Köhler, F.3    Herges, R.4
  • 32
    • 27744606394 scopus 로고    scopus 로고
    • The Magnetic Shielding Function of Molecules and Pi-Electron Delocalization
    • Heine, T.; Corminboeuf, C.; Seifert, G. The Magnetic Shielding Function of Molecules and Pi-Electron Delocalization. Chem. Rev. 2005, 105, 3889-3910.
    • (2005) Chem. Rev. , vol.105 , pp. 3889-3910
    • Heine, T.1    Corminboeuf, C.2    Seifert, G.3
  • 33
    • 27744481399 scopus 로고    scopus 로고
    • Theoretical Evaluation of Electron Delocalization in Aromatic Molecules by Means of Atoms in Molecules (AIM) and Electron Localization Function (ELF) Topological Approaches
    • Poater, J.; Duran, M.; Solà, M.; Silvi, B. Theoretical Evaluation of Electron Delocalization in Aromatic Molecules by Means of Atoms in Molecules (AIM) and Electron Localization Function (ELF) Topological Approaches. Chem. Rev. 2005, 105, 3911-3947.
    • (2005) Chem. Rev. , vol.105 , pp. 3911-3947
    • Poater, J.1    Duran, M.2    Solà, M.3    Silvi, B.4
  • 34
    • 0035353538 scopus 로고    scopus 로고
    • Aromaticity and Ring Currents
    • Gomes, J.A.N.F.; Mallion, R.B. Aromaticity and Ring Currents. Chem. Rev. 2001, 101, 1349-1384.
    • (2001) Chem. Rev. , vol.101 , pp. 1349-1384
    • Gomes, J.A.N.F.1    Mallion, R.B.2
  • 35
    • 33947315480 scopus 로고
    • Diamagnetic Susceptibility Eexaltation as a Criterion of Aromaticity
    • Dauben, H.J., Jr.; Wilson, J.D.; Laity, J.L. Diamagnetic Susceptibility Eexaltation as a Criterion of Aromaticity. J. Am. Chem. Soc. 1968, 90, 811-813.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 811-813
    • Dauben Jr., H.J.1    Wilson, J.D.2    Laity, J.L.3
  • 36
    • 33947299620 scopus 로고
    • Diamagnetic Susceptibility Exaltation in Hydrocarbons
    • Dauben, H.J., Jr.; Wilson, J.D.; Laity, J.L. Diamagnetic Susceptibility Exaltation in Hydrocarbons. J. Am. Chem. Soc. 1969, 91, 1991-1998.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 1991-1998
    • Dauben Jr., H.J.1    Wilson, J.D.2    Laity, J.L.3
  • 37
    • 27744530363 scopus 로고    scopus 로고
    • Nucleus-Independent Chemical Shifts (NICS) as an Aromaticity Criterion
    • Chen, Z.; Wannere, C.S.; Corminboeuf, C.; Puchta, R.; Schleyer, P.v.R. Nucleus-Independent Chemical Shifts (NICS) as an Aromaticity Criterion. Chem. Rev. 2005, 105, 3842-3888.
    • (2005) Chem. Rev. , vol.105 , pp. 3842-3888
    • Chen, Z.1    Wannere, C.S.2    Corminboeuf, C.3    Puchta, R.4    Schleyer, P.V.R.5
  • 39
    • 0000197433 scopus 로고
    • Calculation of Magnetic Response Properties using a Continuous Set of Gauge Transformations
    • Keith, T.A.; Bader, R.F.W. Calculation of Magnetic Response Properties using a Continuous Set of Gauge Transformations. Chem. Phys. Lett. 1993, 210, 223-231.
    • (1993) Chem. Phys. Lett. , vol.210 , pp. 223-231
    • Keith, T.A.1    Bader, R.F.W.2
  • 40
    • 0001560524 scopus 로고
    • On CHF Calculations of Second-Order Magnetic Properties using the Method of Continuous Ttransformation of Origin of the Current Density
    • Coriani, S.; Lazzeretti, P.; Malagoli, M.; Zanasi, R. On CHF Calculations of Second-Order Magnetic Properties using the Method of Continuous Ttransformation of Origin of the Current Density. Theor. Chim. Acta 1994, 89, 181-192.
    • (1994) Theor. Chim. Acta , vol.89 , pp. 181-192
    • Coriani, S.1    Lazzeretti, P.2    Malagoli, M.3    Zanasi, R.4
  • 41
    • 84860430386 scopus 로고    scopus 로고
    • A related review was reported in 2001
    • A related review was reported in 2001
  • 42
    • 0035813898 scopus 로고    scopus 로고
    • About the Antiaromaticity of Planar Cyclooctatetraene
    • Klärner, F.-G. About the Antiaromaticity of Planar Cyclooctatetraene. Angew. Chem. Int. Ed. 2001, 40, 3977-3981.
    • (2001) Angew. Chem. Int. Ed. , vol.40 , pp. 3977-3981
    • Klärner, F.-G.1
  • 45
    • 76149121794 scopus 로고    scopus 로고
    • Cyclooctatetraenes
    • Nishinaga, T. Cyclooctatetraenes. Sci. Synth. 2009, 45a, 383-406.
    • (2009) Sci. Synth. , vol.45 a , pp. 383-406
    • Nishinaga, T.1
  • 46
    • 0344588866 scopus 로고    scopus 로고
    • Consequences of Triplet Aromaticity in 4nπ-Electron Annulenes: Calculation of Magnetic Shieldings for Open-Shell Species
    • Gogonea, V.; Schleyer, P.v.R.; Schreiner, P.R. Consequences of Triplet Aromaticity in 4nπ-Electron Annulenes: Calculation of Magnetic Shieldings for Open-Shell Species. Angew. Chem. Int. Ed. 1998, 37, 1945-1948.
    • (1998) Angew. Chem. Int. Ed. , vol.37 , pp. 1945-1948
    • Gogonea, V.1    Schleyer, P.2    Schreiner, P.V.R.3
  • 47
    • 58149214158 scopus 로고    scopus 로고
    • Aromaticity and Antiaromaticity in the Low-Lying Electronic States of Cyclooctatetraene
    • Karadakov, P.B. Aromaticity and Antiaromaticity in the Low-Lying Electronic States of Cyclooctatetraene. J. Phys. Chem. A 2008, 112, 12707-12713.
    • (2008) J. Phys. Chem. A , vol.112 , pp. 12707-12713
    • Karadakov, P.B.1
  • 48
    • 0037071716 scopus 로고    scopus 로고
    • Planarization of 1,3,5,7-Cyclooctatetraene as a Result of a Partial Rehybridization at Carbon Atoms: an MP2/6-31G* and B3LYP/6-311G** Study
    • Krygowski, T.M.; Pindelska, E.; Cyrański, M.K.; Häfelinger, G. Planarization of 1,3,5,7-Cyclooctatetraene as a Result of a Partial Rehybridization at Carbon Atoms: an MP2/6-31G* and B3LYP/6-311G** Study. Chem. Phys. Lett. 2002, 359, 158-162.
    • (2002) Chem. Phys. Lett. , vol.359 , pp. 158-162
    • Krygowski, T.M.1    Pindelska, E.2    Cyrański, M.K.3    Häfelinger, G.4
  • 49
    • 76149084210 scopus 로고    scopus 로고
    • Cyclic Tetrathiophenes Planarized by Silicon and Sulfur Bridges Bearing Antiaromatic Cyclooctatetraene Core: Syntheses, Structures, and Properties
    • Ohmae, T.; Nishinaga, T.; Wu, M.; Iyoda, M. Cyclic Tetrathiophenes Planarized by Silicon and Sulfur Bridges Bearing Antiaromatic Cyclooctatetraene Core: Syntheses, Structures, and Properties. J. Am. Chem. Soc. 2010, 132, 1066-1074.
    • (2010) J. Am. Chem. Soc. , vol.132 , pp. 1066-1074
    • Ohmae, T.1    Nishinaga, T.2    Wu, M.3    Iyoda, M.4
  • 50
    • 0001290462 scopus 로고
    • 3ππ* State of Cyclic Hydrocarbons
    • 3ππ* State of Cyclic Hydrocarbons. J. Am. Chem. Soc. 1972, 94, 4941-4948.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 4941-4948
    • Baird, N.C.1
  • 51
    • 0009673330 scopus 로고
    • Aromaticity-Based Theory of Pericyclic Reactions
    • Aihara, J. Aromaticity-Based Theory of Pericyclic Reactions. Bull. Chem. Soc. Jpn. 1978, 51, 1788-1792.
    • (1978) Bull. Chem. Soc. Jpn. , vol.51 , pp. 1788-1792
    • Aihara, J.1
  • 52
    • 0343202083 scopus 로고
    • Geometry of Triplets and Dianions of Aromatic and Antiaromatic Systems
    • Jug, K.; Malar, E.J.P. Geometry of Triplets and Dianions of Aromatic and Antiaromatic Systems. J. Mol. Struct. (THEOCHEM) 1987, 153, 221-226.
    • (1987) J. Mol. Struct. (THEOCHEM) , vol.153 , pp. 221-226
    • Jug, K.1    Malar, E.J.P.2
  • 53
    • 32144434172 scopus 로고    scopus 로고
    • Nucleus-Independent Chemical Shifts (NICS): Distance Dependence and Revised Criteria for Aromaticity and Antiaromaticity
    • Stanger, A. Nucleus-Independent Chemical Shifts (NICS): Distance Dependence and Revised Criteria for Aromaticity and Antiaromaticity. J. Org. Chem. 2006, 71, 883-893.
    • (2006) J. Org. Chem. , vol.71 , pp. 883-893
    • Stanger, A.1
  • 54
    • 0035824045 scopus 로고    scopus 로고
    • Four- and Two-Electron Rules for Diatropic and Paratropic Ring Currents in Monocyclic π-Systems
    • Steiner, E.; Fowler, P.W. Four- and Two-Electron Rules for Diatropic and Paratropic Ring Currents in Monocyclic π-Systems. Chem. Commun. 2001, 2220-2221.
    • (2001) Chem. Commun. , pp. 2220-2221
    • Steiner, E.1    Fowler, P.W.2
  • 55
    • 33846054085 scopus 로고    scopus 로고
    • Full Spectral Decomposition of Ring Currents
    • Steiner, E.; Soncini, A.; Fowler, P.W. Full Spectral Decomposition of Ring Currents. J. Phys. Chem. A 2006, 110, 12882-12886.
    • (2006) J. Phys. Chem. A , vol.110 , pp. 12882-12886
    • Steiner, E.1    Soncini, A.2    Fowler, P.W.3
  • 56
    • 33645914789 scopus 로고    scopus 로고
    • Persistence of Paratropic Ring Currents in Nonplanar, Tub-Shaped Geometries of 1,3,5,7-Cyclooctatetraene
    • Havenith, R.A.; Fowler, P.W.; Jenneskens, L.W. Persistence of Paratropic Ring Currents in Nonplanar, Tub-Shaped Geometries of 1,3,5,7-Cyclooctatetraene. Org. Lett. 2006, 8, 1255-1258.
    • (2006) Org. Lett. , vol.8 , pp. 1255-1258
    • Havenith, R.A.1    Fowler, P.W.2    Jenneskens, L.W.3
  • 57
    • 0001627373 scopus 로고
    • Unsaturated Eight-Membered Ring Compounds. XI. Synthesis of sym-Dibenzo-1,5-cyclooctadiene-3,7-diyne and sym-Dibenzo-1,3,5- cyclooctatrien-7-yne. Presumably Planar Conjugated Eight-Membered Ring Compounds
    • Wong, H.N.C.; Garratt, P.J.; Sondheimer, F. Unsaturated Eight-Membered Ring Compounds. XI. Synthesis of sym-Dibenzo-1,5-cyclooctadiene-3,7-diyne and sym-Dibenzo-1,3,5- cyclooctatrien-7-yne, Presumably Planar Conjugated Eight-Membered Ring Compounds. J. Am. Chem. Soc. 1974, 96, 5604-5605.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 5604-5605
    • Wong, H.N.C.1    Garratt, P.J.2    Sondheimer, F.3
  • 58
    • 1542652096 scopus 로고
    • Synthesis and Reactions of 5,6,11,12-Tetradehydrodibenzo[a,e]cyclooctene and 5,6-Didehydrodibenzo[a,e]cyclooctene
    • Wong, H.N.C.; Sondheimer, F. Synthesis and Reactions of 5,6,11,12-Tetradehydrodibenzo[a,e]cyclooctene and 5,6-Didehydrodibenzo[a,e]cyclooctene. Tetrahedron 1981, 37, 99-109.
    • (1981) Tetrahedron , vol.37 , pp. 99-109
    • Wong, H.N.C.1    Sondheimer, F.2
  • 59
    • 0003036847 scopus 로고
    • The Planar Dehydro[8]annulenes
    • Huang, N.Z.; Sondheimer, F. The Planar Dehydro[8]annulenes. Acc. Chem. Res. 1982, 15, 96-102.
    • (1982) Acc. Chem. Res. , vol.15 , pp. 96-102
    • Huang, N.Z.1    Sondheimer, F.2
  • 60
    • 0001420026 scopus 로고
    • Crystal structure of 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctene (sym-dibenzo-1,5-cyclooctadiene-3.7-diyne)
    • Destro, R.; Pilati, T.; Simonetta, M. Crystal structure of 5,6,11,12-tetradehydrodibenzo[a,e]cyclooctene (sym-dibenzo-1,5-cyclooctadiene-3,7-diyne). J. Am. Chem. Soc. 1975, 97, 658-659.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 658-659
    • Destro, R.1    Pilati, T.2    Simonetta, M.3
  • 63
    • 33947296450 scopus 로고
    • Unsaturated 8-Membered Ring Compounds. VIII. Photochemistry of 7,8-Dimethylene-1,3,5-cyclooctatrienes. Synthesis of Bicyclo[6. 2. 0]deca-1,3,5,7-tetraene
    • Elix, J.A.; Sargent, M.V.; Sondheimer, F. Unsaturated 8-Membered Ring Compounds. VIII. Photochemistry of 7,8-Dimethylene-1,3,5-cyclooctatrienes. Synthesis of Bicyclo[6.2.0]deca-1,3,5,7-tetraene. J. Am. Chem. Soc. 1970, 92, 969-973.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 969-973
    • Elix, J.A.1    Sargent, M.V.2    Sondheimer, F.3
  • 64
    • 0001091463 scopus 로고
    • Synthesis, Structure, and Properties of a 2-(Trimethylsilyl) cyclobutenocyclooctatetraene
    • Pirrung, M.C.; Krishnamurthy, N.; Nunn, D. S.; McPhail, A. T. Synthesis, Structure, and Properties of a 2-(Trimethylsilyl)cyclobutenocyclooctatetraene. J. Am. Chem. Soc. 1991, 113, 4910-4917.
    • (1991) J. Am. Chem. Soc. , vol.113 , pp. 4910-4917
    • Pirrung, M.C.1    Krishnamurthy, N.2    Nunn, D.S.3    McPhail, A.T.4
  • 65
    • 2142797376 scopus 로고
    • Flattening of the Cyclooctatetraene Ring by Annulation
    • Paquette, L.A.; Wang, T.Z.; Cottrell, C.E. Flattening of the Cyclooctatetraene Ring by Annulation. J. Am. Chem. Soc. 1987, 109, 3730-3734.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 3730-3734
    • Paquette, L.A.1    Wang, T.Z.2    Cottrell, C.E.3
  • 66
    • 0000188953 scopus 로고
    • The Synthesis of Bicyclo[6.2.0]decapentaene
    • Oda, M.; Oikawa, H. The Synthesis of Bicyclo[6.2.0]decapentaene. Tetrahedron Lett. 1980, 21, 107-110.
    • (1980) Tetrahedron Lett , vol.21 , pp. 107-110
    • Oda, M.1    Oikawa, H.2
  • 67
    • 0006693543 scopus 로고
    • Crystal and Molecular Structure of 9,10-Diphenylbicyclo[6. 2. 0]decapentaene a 10 π Aromatic Compound
    • Kabuto, C.; Oda, M. Crystal and Molecular Structure of 9,10-Diphenylbicyclo[6.2.0]decapentaene a 10 π Aromatic Compound. Tetrahedron Lett. 1980, 21, 103-106.
    • (1980) Tetrahedron Lett , vol.21 , pp. 103-106
    • Kabuto, C.1    Oda, M.2
  • 71
    • 0000163113 scopus 로고
    • Planarization of Unsaturated Rings. Cycloheptatriene with a Planar Seven-Membered Ring
    • Ermer, O.; Klärner, F.-G.; Wette, M. Planarization of Unsaturated Rings. Cycloheptatriene with a Planar Seven-Membered Ring. J. Am. Chem. Soc. 1986, 108, 4908-4911.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 4908-4911
    • Ermer, O.1    Klärner, F.-G.2    Wette, M.3
  • 72
    • 0032989140 scopus 로고    scopus 로고
    • Pressure-Induced Cycloadditions of Dicyanoacetylene to Strained Arenes: The Formation of Cyclooctatetraene, 9,10-Dihydronaphthalene, and Azulene Derivatives; A Degenerate [1,5] Sigmatropic Shift - Comparison between Theory and Experiment
    • Klärner, F.-G.; Ehrhardt, R.; Bandmann, H.; Boese, R.; Bläser, D.; Houk, K.N.; Beno, B.R. Pressure-Induced Cycloadditions of Dicyanoacetylene to Strained Arenes: The Formation of Cyclooctatetraene, 9,10-Dihydronaphthalene, and Azulene Derivatives; A Degenerate [1,5] Sigmatropic Shift - Comparison between Theory and Experiment. Chem. Eur. J. 1999, 5, 2119-2132.
    • (1999) Chem. Eur. J. , vol.5 , pp. 2119-2132
    • Klärner, F.-G.1    Ehrhardt, R.2    Bandmann, H.3    Boese, R.4    Bläser, D.5    Houk, K.N.6    Beno, B.R.7
  • 73
    • 0009071180 scopus 로고
    • Preparation of Cycloocta[def]biphenylene, a Novel Benzenoid Antiaromatic Hydrocarbon
    • Wilcox, C.F., Jr.; Uetrecht, J.P.; Grohman, K.K. Preparation of Cycloocta[def]biphenylene, a Novel Benzenoid Antiaromatic Hydrocarbon. J. Am. Chem. Soc. 1972, 94, 2532-2533.
    • (1972) J. Am. Chem. Soc. , vol.94 , pp. 2532-2533
    • Wilcox Jr., C.F.1    Uetrecht, J.P.2    Grohman, K.K.3
  • 74
    • 33847800716 scopus 로고
    • Synthesis and Properties of Cycloocta[def]biphenylene, a Stable Benzenoid Paratropic Hydrocarbon
    • Wilcox, C.F., Jr.; Uetrecht, J.P.; Grantham, G.D.; Grohmann, K.G. Synthesis and Properties of Cycloocta[def]biphenylene, a Stable Benzenoid Paratropic Hydrocarbon. J. Am. Chem. Soc. 1975, 97, 1914-1920.
    • (1975) J. Am. Chem. Soc. , vol.97 , pp. 1914-1920
    • Wilcox Jr., C.F.1    Uetrecht, J.P.2    Grantham, G.D.3    Grohmann, K.G.4
  • 75
    • 0000611005 scopus 로고
    • Cycloocta[def]fluorene: a Planar Cyclooctatetraene Derivative. Paratropicity of Hydrocarbon and Anion
    • Willner, I.; Rabinovitz, M. Cycloocta[def]fluorene: a Planar Cyclooctatetraene Derivative. Paratropicity of Hydrocarbon and Anion. J. Org. Chem. 1980, 45, 1628-1633.
    • (1980) J. Org. Chem. , vol.45 , pp. 1628-1633
    • Willner, I.1    Rabinovitz, M.2
  • 76
    • 84981915255 scopus 로고
    • Cyclooctatetraene Systems Flattened by Steric Constraints
    • Hellwinkel, D.; Reiff, G. Cyclooctatetraene Systems Flattened by Steric Constraints. Angew. Chem., Int. Ed. Engl. 1970, 9, 527-528.
    • (1970) Angew. Chem., Int. Ed. Engl. , vol.9 , pp. 527-528
    • Hellwinkel, D.1    Reiff, G.2
  • 77
    • 2942546641 scopus 로고    scopus 로고
    • Soluble Cycloannulated Tetroxa[8]circulane Derivatives: Synthesis, Optical and Electrochemical Properties, and Generation of Their Robust Cation-Radical Salts
    • Rathore, R.; Abdelwahed, S.H. Soluble Cycloannulated Tetroxa[8]circulane Derivatives: Synthesis, Optical and Electrochemical Properties, and Generation of Their Robust Cation-Radical Salts. Tetrahedron Lett. 2004, 45, 5267-5270.
    • (2004) Tetrahedron Lett , vol.45 , pp. 5267-5270
    • Rathore, R.1    Abdelwahed, S.H.2
  • 78
    • 0001703197 scopus 로고
    • Copper Coupling of 1-Chloro-2-iodo- and 1,2-Diiodoperfluorocycloalkenes
    • Soulen, R.L.; Choi, S.K.; Park, J.D. Copper Coupling of 1-Chloro-2-iodo- and 1,2-Diiodoperfluorocycloalkenes. J. Fluorine Chem. 1973/74, 3, 141-150.
    • (1973) J. Fluorine Chem. , vol.3 , pp. 141-150
    • Soulen, R.L.1    Choi, S.K.2    Park, J.D.3
  • 79
    • 37049096428 scopus 로고
    • Perfluorotetracyclobutacyclooctatetraene; a Planar Eight-Memberedring System; X-ray Crystal Structure
    • Einstein, F.W.B.; Willis, A.C.; Cullen, W.R.; Soulen, R.L. Perfluorotetracyclobutacyclooctatetraene; a Planar Eight-Memberedring System; X-ray Crystal Structure. J. Chem. Soc. Chem. Commun. 1981, 526-528.
    • (1981) J. Chem. Soc. Chem. Commun. , pp. 526-528
    • Einstein, F.W.B.1    Willis, A.C.2    Cullen, W.R.3    Soulen, R.L.4
  • 80
    • 0035961493 scopus 로고    scopus 로고
    • Quantum Mechanical Designs toward Planar Delocalized Cyclooctatetraene: A New Target for Synthesis
    • Baldridge, K.K.; Siegel, J.S. Quantum Mechanical Designs toward Planar Delocalized Cyclooctatetraene: A New Target for Synthesis. J. Am. Chem. Soc. 2001, 123, 1755-1759.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 1755-1759
    • Baldridge, K.K.1    Siegel, J.S.2
  • 81
    • 33748505220 scopus 로고    scopus 로고
    • Why Does Perfluorination Render Bicyclo[2.2.0]hex-1(4)-ene Stable toward Dimerization? Calculations Provide the Answers
    • Shelton, G.R.; Hrovat, D.A.; Wei, H.; Borden, W.T. Why Does Perfluorination Render Bicyclo[2.2.0]hex-1(4)-ene Stable toward Dimerization? Calculations Provide the Answers. J. Am. Chem. Soc. 2006, 128, 12020-12027.
    • (2006) J. Am. Chem. Soc. , vol.128 , pp. 12020-12027
    • Shelton, G.R.1    Hrovat, D.A.2    Wei, H.3    Borden, W.T.4
  • 82
    • 0037012742 scopus 로고    scopus 로고
    • Paratropic Delocalized Ring Currents in Flattened Cyclooctatetraene Systems with Bond Alternation
    • Fowler, P.W.; Havenith, R.W.A.; Jenneskens, L.W.; Soncini, A.; Steiner, E. Paratropic Delocalized Ring Currents in Flattened Cyclooctatetraene Systems with Bond Alternation. Angew. Chem. Int. Ed. 2002, 41, 1558-1560.
    • (2002) Angew. Chem. Int. Ed. , vol.41 , pp. 1558-1560
    • Fowler, P.W.1    Havenith, R.W.A.2    Jenneskens, L.W.3    Soncini, A.4    Steiner, E.5
  • 83
    • 0011449836 scopus 로고
    • Electrochemistry of Perfluorotetracyclobuta-1,3,5,7-cyclooctatetraene, a Powerful Neutral Organic Oxidant
    • Britton, W.E.; Ferraris, J.P.; Soulen, R.L. Electrochemistry of Perfluorotetracyclobuta-1,3,5,7-cyclooctatetraene, a Powerful Neutral Organic Oxidant. J. Am. Chem. Soc. 1982, 104, 5322-5325.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 5322-5325
    • Britton, W.E.1    Ferraris, J.P.2    Soulen, R.L.3
  • 84
    • 0035961533 scopus 로고    scopus 로고
    • Efficient Synthesis of Benzene and Planar Cyclooctatetraene Fully Annelated with Bicyclo[2.1.1]hex-2-ene
    • Matsuura, A.; Komatsu, K. Efficient Synthesis of Benzene and Planar Cyclooctatetraene Fully Annelated with Bicyclo[2.1.1]hex-2-ene. J. Am. Chem. Soc. 2001, 123, 1768-1769.
    • (2001) J. Am. Chem. Soc. , vol.123 , pp. 1768-1769
    • Matsuura, A.1    Komatsu, K.2
  • 85
    • 53849118166 scopus 로고    scopus 로고
    • Antiaromaticity and Reactivity of a Planar Cyclooctatetraene Fully Annelated with Bicyclo[2.1.1]hexane Units
    • Nishinaga, T.; Uto, T.; Inoue, R.; Matsuura, A.; Treitel, N.; Rabinoviz, M.; Komatsu, K. Antiaromaticity and Reactivity of a Planar Cyclooctatetraene Fully Annelated with Bicyclo[2.1.1]hexane Units. Chem. Eur. J. 2008, 14, 2067-2074.
    • (2008) Chem. Eur. J. , vol.14 , pp. 2067-2074
    • Nishinaga, T.1    Uto, T.2    Inoue, R.3    Matsuura, A.4    Treitel, N.5    Rabinoviz, M.6    Komatsu, K.7
  • 86
    • 10044242586 scopus 로고    scopus 로고
    • Novel Cyclooctatetraene Radical Cation Planarized by Full Annelation with Bicyclo[2.1.1]hexene Units
    • Nishinaga, T.; Uto, T.; Komatsu, K. Novel Cyclooctatetraene Radical Cation Planarized by Full Annelation with Bicyclo[2.1.1]hexene Units. Org. Lett. 2004, 6, 4611-4614.
    • (2004) Org. Lett. , vol.6 , pp. 4611-4614
    • Nishinaga, T.1    Uto, T.2    Komatsu, K.3
  • 87
    • 0000450727 scopus 로고
    • First X-ray Structure of a Cyclooctatetraene Cation Radical: the Hexachloroantimonate of the Tetrakis(bicyclo[2.2.2]octeno)cyclooctatetraene Cation Radical
    • Nishinaga, T.; Komatsu, K.; Sugita, N.; Lindner, H.J.; Richter, J. First X-ray Structure of a Cyclooctatetraene Cation Radical: the Hexachloroantimonate of the Tetrakis(bicyclo[2.2.2]octeno)cyclooctatetraene Cation Radical. J. Am. Chem. Soc. 1993, 115, 11642-11643.
    • (1993) J. Am. Chem. Soc. , vol.115 , pp. 11642-11643
    • Nishinaga, T.1    Komatsu, K.2    Sugita, N.3    Lindner, H.J.4    Richter, J.5
  • 89
    • 55049132223 scopus 로고    scopus 로고
    • Synthesis and Characterizations of Free Base and Cu(II) Complex of a Porphyrin Sheet
    • Nakamura, Y.; Aratani, N.; Furukawa, K.; Osuka, A. Synthesis and Characterizations of Free Base and Cu(II) Complex of a Porphyrin Sheet. Tetrahedron 2008, 64, 11433-11439.
    • (2008) Tetrahedron , vol.64 , pp. 11433-11439
    • Nakamura, Y.1    Aratani, N.2    Furukawa, K.3    Osuka, A.4
  • 90
    • 34447323593 scopus 로고    scopus 로고
    • Experimental and Theoretical Investigations into the Paratropic Ring Current of a Porphyrin Sheet
    • Nakamura, Y.; Aratani, N.; Osuka, A. Experimental and Theoretical Investigations into the Paratropic Ring Current of a Porphyrin Sheet. Chem. Asian. J. 2007, 2, 860-866.
    • (2007) Chem. Asian. J. , vol.2 , pp. 860-866
    • Nakamura, Y.1    Aratani, N.2    Osuka, A.3
  • 92
    • 34548162137 scopus 로고    scopus 로고
    • Are Antiaromatic Rings Stacked Face-to-Face Aromatic?
    • Corminboeuf, C.; Schleyer, P.v.R.; Warner, P. Are Antiaromatic Rings Stacked Face-to-Face Aromatic? Org. Lett. 2007, 9, 3263-3266.
    • (2007) Org. Lett. , vol.9 , pp. 3263-3266
    • Corminboeuf, C.1    Schleyer, P.V.R.2    Warner, P.3
  • 93
    • 27744560565 scopus 로고    scopus 로고
    • Möbius Aromaticity and Delocalization
    • Rzepa, H.S. Möbius Aromaticity and Delocalization. Chem. Rev. 2005, 105, 3697-3715.
    • (2005) Chem. Rev. , vol.105 , pp. 3697-3715
    • Rzepa, H.S.1
  • 94
    • 67949118648 scopus 로고    scopus 로고
    • Möbius Aromaticity and Antiaromaticity in Expanded Porphyrins
    • Yoon, Z.S.; Osuka, A.; Kim, D. Möbius Aromaticity and Antiaromaticity in Expanded Porphyrins. Nature Chem. 2009, 1, 113-122.
    • (2009) Nature Chem , vol.1 , pp. 113-122
    • Yoon, Z.S.1    Osuka, A.2    Kim, D.3
  • 95
    • 60949086971 scopus 로고    scopus 로고
    • Stacked-Ring Aromaticity: An Orbital Model
    • Bean, D.E.; Fowler, P. W. Stacked-Ring Aromaticity: An Orbital Model. Org. Lett. 2008, 10, 5573-5576.
    • (2008) Org. Lett. , vol.10 , pp. 5573-5576
    • Bean, D.E.1    Fowler, P.W.2
  • 96
    • 67649858837 scopus 로고    scopus 로고
    • Origin of Stacked-Ring Aromaticity
    • Aihara, J.-i. Origin of Stacked-Ring Aromaticity. J. Phys. Chem. A 2009, 113, 7945-7952.
    • (2009) J. Phys. Chem. A , vol.113 , pp. 7945-7952
    • Aihara, J.-I.1


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