메뉴 건너뛰기




Volumn 1, Issue 2, 2011, Pages 172-190

The Cope rearrangement-the first born of a great family

Author keywords

[No Author keywords available]

Indexed keywords

ANALOGOUS REACTIONS; COPE REARRANGEMENT; ELECTROCYCLIC REACTIONS; PERICYCLIC REACTION; THEORETICAL INVESTIGATIONS; THEORETICAL METHODS; THERMAL REARRANGEMENT; TRANSITION STRUCTURES;

EID: 84863490778     PISSN: 17590876     EISSN: 17590884     Source Type: Journal    
DOI: 10.1002/wcms.17     Document Type: Article
Times cited : (50)

References (124)
  • 1
    • 0000254656 scopus 로고
    • The Cope rearrangement revisited
    • doi: 10.1021/ja00754a042.
    • Hoffmann R, Stohrer W-D. The Cope rearrangement revisited. J Am Chem Soc 1971, 93: 6941-6948. doi: 10.1021/ja00754a042.
    • (1971) J Am Chem Soc , vol.93 , pp. 6941-6948
    • Hoffmann, R.1    Stohrer, W.-D.2
  • 2
    • 3242804842 scopus 로고
    • The mechanism of the Cope rearrangement
    • doi: 10.1021/ja00487a071.
    • Gajewski JJ, Conrad ND. The mechanism of the Cope rearrangement. J Am Chem Soc 1978, 100: 6268-6269. doi: 10.1021/ja00487a071.
    • (1978) J Am Chem Soc , vol.100 , pp. 6268-6269
    • Gajewski, J.J.1    Conrad, N.D.2
  • 3
    • 0000708426 scopus 로고
    • Mechanism of the Cope rearrangement
    • doi: 10.1021/ja00254a001.
    • Dewar MJS, Jie C. Mechanism of the Cope rearrangement. J Am Chem Soc 1987, 109: 5893-5900. doi: 10.1021/ja00254a001.
    • (1987) J Am Chem Soc , vol.109 , pp. 5893-5900
    • Dewar, M.J.S.1    Jie, C.2
  • 4
    • 0001622172 scopus 로고
    • The Cope rearrangement revisited
    • doi: 10.1021/ja00026a007.
    • Dupuis M, Murray C, Davidson ER. The Cope rearrangement revisited. J Am Chem Soc 1991, 113: 9756-9759. doi: 10.1021/ja00026a007.
    • (1991) J Am Chem Soc , vol.113 , pp. 9756-9759
    • Dupuis, M.1    Murray, C.2    Davidson, E.R.3
  • 5
    • 0000729216 scopus 로고    scopus 로고
    • Theoretical secondary kinetic isotope effects and the interpretation of transition state geometries. 1. The Cope rearrangement
    • doi: 10.1021/ja00048a032.
    • Houk KN, Gustafson SM, Black KA. Theoretical secondary kinetic isotope effects and the interpretation of transition state geometries. 1. The Cope rearrangement. J Am Chem Soc 2002, 114: 8565-8572. doi: 10.1021/ja00048a032.
    • (2002) J Am Chem Soc , vol.114 , pp. 8565-8572
    • Houk, K.N.1    Gustafson, S.M.2    Black, K.A.3
  • 6
    • 0012645193 scopus 로고    scopus 로고
    • Claisen, Cope and related rearrangements in the synthesis of flavour and fragrance compounds
    • doi: 10.3390/50801033.
    • Nowicki J. Claisen, Cope and related rearrangements in the synthesis of flavour and fragrance compounds. Molecules 2000, 5: 1033-1050. doi: 10.3390/50801033.
    • (2000) Molecules , vol.5 , pp. 1033-1050
    • Nowicki, J.1
  • 7
    • 45449094668 scopus 로고    scopus 로고
    • Microwave-assisted Claisen and aza-Claisen rearrangements
    • doi: 10.2174/157019308784223587.
    • Tymoshenko DO. Microwave-assisted Claisen and aza-Claisen rearrangements. Mini-Rev Org Chem 2008, 5: 85-95. doi: 10.2174/157019308784223587.
    • (2008) Mini-Rev Org Chem , vol.5 , pp. 85-95
    • Tymoshenko, D.O.1
  • 8
    • 33845471185 scopus 로고
    • Catalysis of the Cope and Claisen rearrangements
    • doi: 10.1021/cr00061a001.
    • Lutz RP. Catalysis of the Cope and Claisen rearrangements. Chem Rev 1984, 84: 205-247. doi: 10.1021/cr00061a001.
    • (1984) Chem Rev , vol.84 , pp. 205-247
    • Lutz, R.P.1
  • 9
    • 85082586002 scopus 로고
    • The hetero-Cope rearrangement in organic synthesis
    • doi: 10.1055/s-1989-27158.
    • Blechert S. The hetero-Cope rearrangement in organic synthesis. Synthesis 1989, 71-82. doi: 10.1055/s-1989-27158.
    • (1989) Synthesis , pp. 71-82
    • Blechert, S.1
  • 10
    • 0345164070 scopus 로고
    • Pericyclic key reactions in biological systems and biomimetic syntheses
    • doi: 10.1039/CS9942300409.
    • Pindur U, Schneider GH. Pericyclic key reactions in biological systems and biomimetic syntheses. Chem Soc Rev 1994, 23: 409-415. doi: 10.1039/CS9942300409.
    • (1994) Chem Soc Rev , vol.23 , pp. 409-415
    • Pindur, U.1    Schneider, G.H.2
  • 12
    • 0035955522 scopus 로고    scopus 로고
    • The Cope rearrangement in theoretical retrospect
    • doi: 10.1016/S0166-1280(01)00536-X.
    • Staroverov VN, Davidson ER. The Cope rearrangement in theoretical retrospect. J Mol Struct (THEOCHEM) 2001, 573: 81-89. doi: 10.1016/S0166-1280(01)00536-X.
    • (2001) J Mol Struct (THEOCHEM) , vol.573 , pp. 81-89
    • Staroverov, V.N.1    Davidson, E.R.2
  • 13
    • 0001373143 scopus 로고
    • Synchronicity in multibond reactions
    • doi: 10.1146/annurev.pc.39.100188.001241.
    • Borden WT, Loncharich RJ, Houk KN. Synchronicity in multibond reactions. Ann Rev Phys Chem 1988, 39: 213-236. doi: 10.1146/annurev.pc.39.100188.001241.
    • (1988) Ann Rev Phys Chem , vol.39 , pp. 213-236
    • Borden, W.T.1    Loncharich, R.J.2    Houk, K.N.3
  • 14
    • 30244518651 scopus 로고    scopus 로고
    • Exploration of pericyclic reaction transition structures by quantum mechanical methods: competing concerted and stepwise mechanisms
    • 169-179. doi: 10.1016/S0166-1280(96)04970-6.
    • Houk KN, Beno BR, Nendel M, Black K, Yoo HY, Wilsey S, Lee JK. Exploration of pericyclic reaction transition structures by quantum mechanical methods: competing concerted and stepwise mechanisms. J Mol Struct (THEOCHEM) 1997, 398-399: 169-179. doi: 10.1016/S0166-1280(96)04970-6.
    • (1997) J Mol Struct (THEOCHEM) , pp. 398-399
    • Houk, K.N.1    Beno, B.R.2    Nendel, M.3    Black, K.4    Yoo, H.Y.5    Wilsey, S.6    Lee, J.K.7
  • 15
    • 0348233443 scopus 로고    scopus 로고
    • A standard set of pericyclic reactions of hydrocarbons for the benchmarking of computational methods: the performance of ab initio, density functional, CASSCF, CASPT2, and CBS-QB3 methods for the prediction of activation barriers, reaction energetics, and transition state geometries
    • doi: 10.1021/jp035501w.
    • Guner V, Khuong KS, Leach AG, Lee PS, Bartberger MD, Houk KN. A standard set of pericyclic reactions of hydrocarbons for the benchmarking of computational methods: the performance of ab initio, density functional, CASSCF, CASPT2, and CBS-QB3 methods for the prediction of activation barriers, reaction energetics, and transition state geometries. J Phys Chem A 2003, 107: 11445-11459. doi: 10.1021/jp035501w.
    • (2003) J Phys Chem A , vol.107 , pp. 11445-11459
    • Guner, V.1    Khuong, K.S.2    Leach, A.G.3    Lee, P.S.4    Bartberger, M.D.5    Houk, K.N.6
  • 16
    • 33947486728 scopus 로고
    • Orbital symmetries and orientational effects in a sigmatropic reaction
    • doi: 10.1021/ja00947a034.
    • Hoffmann R, Woodward RB. Orbital symmetries and orientational effects in a sigmatropic reaction. J Am Chem Soc 1965, 87: 4389-4390. doi: 10.1021/ja00947a034.
    • (1965) J Am Chem Soc , vol.87 , pp. 4389-4390
    • Hoffmann, R.1    Woodward, R.B.2
  • 17
    • 0004752157 scopus 로고
    • Stereospecificity with reference to some cyclic reactions
    • doi: 10.1016/S0040-4039(01)83901-0.
    • Fukui K. Stereospecificity with reference to some cyclic reactions. Tetrahedron Lett 1965, 6: 2009-2015. doi: 10.1016/S0040-4039(01)83901-0.
    • (1965) Tetrahedron Lett , vol.6 , pp. 2009-2015
    • Fukui, K.1
  • 18
    • 12344289470 scopus 로고    scopus 로고
    • Computational studies on the cyclizations of enediynes, enyne-allenes, and related polyunsaturated systems
    • doi: 10.1021/ar020270h.
    • Schreiner PR, Navarro-Vazquez A, Prall M. Computational studies on the cyclizations of enediynes, enyne-allenes, and related polyunsaturated systems. Acc Chem Res 2005, 38: 29-37. doi: 10.1021/ar020270h.
    • (2005) Acc Chem Res , vol.38 , pp. 29-37
    • Schreiner, P.R.1    Navarro-Vazquez, A.2    Prall, M.3
  • 19
    • 4444308034 scopus 로고    scopus 로고
    • Cope reaction families: to be or not to be a biradical
    • doi: 10.1021/ol0488340.
    • Schreiner PR, Navarro-Vásquez A, Prall M. Cope reaction families: to be or not to be a biradical. Org Lett 2004, 6: 2981-2984. doi: 10.1021/ol0488340.
    • (2004) Org Lett , vol.6 , pp. 2981-2984
    • Schreiner, P.R.1    Navarro-Vásquez, A.2    Prall, M.3
  • 20
    • 0032540659 scopus 로고    scopus 로고
    • Alkynes, allenes, and alkenes in [3,3]-sigmatropy: functional diversity and kinetic monotony. A theoretical analysis
    • doi: 10.1021/ja972826f.
    • Black KA, Wilsey S, Houk KN. Alkynes, allenes, and alkenes in [3, 3]-sigmatropy: functional diversity and kinetic monotony. A theoretical analysis. J Am Chem Soc 1998, 120: 5622-5627. doi: 10.1021/ja972826f.
    • (1998) J Am Chem Soc , vol.120 , pp. 5622-5627
    • Black, K.A.1    Wilsey, S.2    Houk, K.N.3
  • 21
    • 0000135746 scopus 로고
    • The introduction of substituted vinyl groups-a rearrangement involving the migration of an allyl group in a three-carbon system
    • doi: 10.1021/ja01859a055.
    • Cope AC, Hardy EM. The introduction of substituted vinyl groups-a rearrangement involving the migration of an allyl group in a three-carbon system. J Am Chem Soc 1940, 62: 441-444. doi: 10.1021/ja01859a055.
    • (1940) J Am Chem Soc , vol.62 , pp. 441-444
    • Cope, A.C.1    Hardy, E.M.2
  • 22
    • 0001940234 scopus 로고
    • The overlap of two allyl radicals or a four-centered transition state in the Cope rearrangement
    • doi: 10.1016/0040-4020(62)80025-8.
    • Doering WvE, Roth WR. The overlap of two allyl radicals or a four-centered transition state in the Cope rearrangement. Tetrahedron 1962, 18: 67-74. doi: 10.1016/0040-4020(62)80025-8.
    • (1962) Tetrahedron , vol.18 , pp. 67-74
    • Doering, W.1    Roth, W.R.2
  • 23
    • 33947091548 scopus 로고
    • Boat and chair transition states of 1,5-hexadiene
    • doi: 10.1021/ja00775a046.
    • Goldstein MJ, Benzon MS. Boat and chair transition states of 1, 5-hexadiene. J Am Chem Soc 1972, 94: 7147-7149. doi: 10.1021/ja00775a046.
    • (1972) J Am Chem Soc , vol.94 , pp. 7147-7149
    • Goldstein, M.J.1    Benzon, M.S.2
  • 24
    • 33847803330 scopus 로고
    • Competitive dissociation and rearrangements of 1,5-hexadiene
    • doi: 10.1021/ja00830a035.
    • Goldstein MJ, DeCamp MR. Competitive dissociation and rearrangements of 1, 5-hexadiene. J Am Chem Soc 1974, 96: 7356-7358. doi: 10.1021/ja00830a035.
    • (1974) J Am Chem Soc , vol.96 , pp. 7356-7358
    • Goldstein, M.J.1    DeCamp, M.R.2
  • 25
    • 0012755090 scopus 로고
    • Asymmetric induction in the Cope rearrangement
    • doi: 10.1039/C19670000619.
    • Hill RK, Gilman NW. Asymmetric induction in the Cope rearrangement. Chem Commun 1967: 619-620. doi: 10.1039/C19670000619.
    • (1967) Chem Commun , pp. 619-620
    • Hill, R.K.1    Gilman, N.W.2
  • 26
    • 0030200756 scopus 로고    scopus 로고
    • Asymmetric [3.3]-sigmatropic rearrangements in organic synthesis
    • doi:10.1016/0957-4166(96)00220-0.
    • Enders D, Knopp M, Schiffers R. Asymmetric [3.3]-sigmatropic rearrangements in organic synthesis. Tetrahedron Asymmetry 1996, 7: 1847-1882. doi:10.1016/0957-4166(96)00220-0.
    • (1996) Tetrahedron Asymmetry , vol.7 , pp. 1847-1882
    • Enders, D.1    Knopp, M.2    Schiffers, R.3
  • 27
    • 0001186171 scopus 로고
    • Diastereomeric transition states. Relative energies of the chair and boat reaction pathways in the Cope rearrangement
    • doi: 10.1021/ja00529a045.
    • Shea KJ, Phillips RB. Diastereomeric transition states. Relative energies of the chair and boat reaction pathways in the Cope rearrangement. J Am Chem Soc 1980, 102: 3156-3162. doi: 10.1021/ja00529a045.
    • (1980) J Am Chem Soc , vol.102 , pp. 3156-3162
    • Shea, K.J.1    Phillips, R.B.2
  • 28
    • 0002313438 scopus 로고
    • Recognition of stereochemical paths by orbital interaction
    • doi: 10.1021/ar50038a003.
    • Fukui K. Recognition of stereochemical paths by orbital interaction. Acc Chem Res 1971, 4: 57-64. doi: 10.1021/ar50038a003.
    • (1971) Acc Chem Res , vol.4 , pp. 57-64
    • Fukui, K.1
  • 29
    • 84981778017 scopus 로고
    • The conservation of orbital symmetry
    • doi: 10.1002/anie.196907811.
    • Woodward RB, Hoffmann R. The conservation of orbital symmetry. Angew Chem Int Ed 1969, 8: 781-932. doi: 10.1002/anie.196907811.
    • (1969) Angew Chem Int Ed , vol.8 , pp. 781-932
    • Woodward, R.B.1    Hoffmann, R.2
  • 30
    • 84981890433 scopus 로고
    • Aromaticity and pericyclic reactions
    • doi: 10.1002/anie.197107611.
    • Dewar MJS. Aromaticity and pericyclic reactions. Angew Chem Int Ed 1971, 10: 761-776. doi: 10.1002/anie.197107611.
    • (1971) Angew Chem Int Ed , vol.10 , pp. 761-776
    • Dewar, M.J.S.1
  • 31
    • 0001360185 scopus 로고
    • The Cope rearrangement revisited again. Results of ab initio calculations beyond the CASSCF level
    • doi: 10.1021/ja00082a032.
    • Hrovat DA, Morokuma K, Borden WT. The Cope rearrangement revisited again. Results of ab initio calculations beyond the CASSCF level. J Am Chem Soc 1994, 116: 1072-1076. doi: 10.1021/ja00082a032.
    • (1994) J Am Chem Soc , vol.116 , pp. 1072-1076
    • Hrovat, D.A.1    Morokuma, K.2    Borden, W.T.3
  • 32
    • 0000493590 scopus 로고
    • A rapidly reversible degenerate cope rearrangement: bicyclo[5.1.0]octa-2,5-diene
    • doi: 10.1016/S0040-4020(01)99207-5.
    • Doering WvE, Roth WR. A rapidly reversible degenerate cope rearrangement: bicyclo[5.1.0]octa-2, 5-diene. Tetrahedron 1963, 19: 715-737. doi: 10.1016/S0040-4020(01)99207-5.
    • (1963) Tetrahedron , vol.19 , pp. 715-737
    • Doering, W.1    Roth, W.R.2
  • 33
    • 37049043006 scopus 로고    scopus 로고
    • Isolation of a cis-1,2-Divinylcyclopro-pane
    • doi: 10.1039/C19650000226
    • Brown JM. Isolation of a cis-1, 2-Divinylcyclopro-pane. Chem Commun 1965: 226-227. doi: 10.1039/C19650000226
    • Chem Commun , vol.1965 , pp. 226-227
    • Brown, J.M.1
  • 34
    • 84875641243 scopus 로고
    • Cope-Umlagerungen mit dipolaren Zwischenprodukten
    • doi: 10.1002/ange.19760880909.
    • Gompper W, Ulrich W-R. Cope-Umlagerungen mit dipolaren Zwischenprodukten. Angew Chem 1976, 88: 298-300. doi: 10.1002/ange.19760880909.
    • (1976) Angew Chem , vol.88 , pp. 298-300
    • Gompper, W.1    Ulrich, W.-R.2
  • 35
    • 84981836034 scopus 로고
    • Valenzisomerisierung von Cyclodeca-1,5-dien
    • doi: 10.1002/hlca.19630460209.
    • Grob CA, Link H, Schiess PW. Valenzisomerisierung von Cyclodeca-1, 5-dien. Helv Chim Acta 1963, 46: 483-492. doi: 10.1002/hlca.19630460209.
    • (1963) Helv Chim Acta , vol.46 , pp. 483-492
    • Grob, C.A.1    Link, H.2    Schiess, P.W.3
  • 36
    • 0000203357 scopus 로고
    • Kinetics of the Cope rearrangement of 1,1-dideuteriohexa-1,5-diene
    • doi: 10.1016/S0040-4020(01)91694-1.
    • Doering WvE, Toscano VG, Beasley GH. Kinetics of the Cope rearrangement of 1, 1-dideuteriohexa-1, 5-diene. Tetrahedron 1971, 27: 5299-5306. doi: 10.1016/S0040-4020(01)91694-1.
    • (1971) Tetrahedron , vol.27 , pp. 5299-5306
    • Doering, W.1    Toscano, V.G.2    Beasley, G.H.3
  • 37
    • 0025374692 scopus 로고
    • A 'frustrated' cope rearrangement: thermal interconversion of 2,6-diphenylhepta-1,6-diene and 1,5-diphenylbicyclo[3.2.0]heptane
    • doi: 10.1021/ja00161a011.
    • Roth WR, Lennartz HW, Doering WvE, Birladeanu L, Guyton CA, Kitagawa T. A 'frustrated' cope rearrangement: thermal interconversion of 2, 6-diphenylhepta-1, 6-diene and 1, 5-diphenylbicyclo[3.2.0]heptane. J Am Chem Soc 1990, 112: 1722-1732. doi: 10.1021/ja00161a011.
    • (1990) J Am Chem Soc , vol.112 , pp. 1722-1732
    • Roth, W.R.1    Lennartz, H.W.2    Doering, W.3    Birladeanu, L.4    Guyton, C.A.5    Kitagawa, T.6
  • 38
    • 33947294958 scopus 로고
    • Thermodynamic and kinetic secondary isotope effects in the Cope rearrangement
    • doi: 10.1021/ja00725a026.
    • Sunko DE, Humski K, Malojcic R, Borcic S. Thermodynamic and kinetic secondary isotope effects in the Cope rearrangement. J Am Chem Soc 1970, 92: 6534-6538. doi: 10.1021/ja00725a026.
    • (1970) J Am Chem Soc , vol.92 , pp. 6534-6538
    • Sunko, D.E.1    Humski, K.2    Malojcic, R.3    Borcic, S.4
  • 39
    • 0001739127 scopus 로고
    • Possible role of 1,4-cyclohexylene intermediates in Cope rearrangements
    • doi: 10.1021/ja00782a078.
    • Dewar MJS, Wade LE. Possible role of 1, 4-cyclohexylene intermediates in Cope rearrangements. J Am Chem Soc 1973, 95: 290-291. doi: 10.1021/ja00782a078.
    • (1973) J Am Chem Soc , vol.95 , pp. 290-291
    • Dewar, M.J.S.1    Wade, L.E.2
  • 40
    • 0001036539 scopus 로고
    • A study of the mechanism of the Cope rearrangement
    • doi: 10.1021/ja00455a034.
    • Dewar MJS, Wade LE. A study of the mechanism of the Cope rearrangement. J Am Chem Soc 1977, 99: 4417-4424. doi: 10.1021/ja00455a034.
    • (1977) J Am Chem Soc , vol.99 , pp. 4417-4424
    • Dewar, M.J.S.1    Wade, L.E.2
  • 41
    • 84984218729 scopus 로고
    • Über den Mechanismus der Cope Umlagerung
    • doi: 10.1002/hlca.19770600422.
    • Wehrli R, Schmid H, Bellus D, Hansen H-J. Über den Mechanismus der Cope Umlagerung. Helv Chim Acta 1977, 60: 1325-1356. doi: 10.1002/hlca.19770600422.
    • (1977) Helv Chim Acta , vol.60 , pp. 1325-1356
    • Wehrli, R.1    Schmid, H.2    Bellus, D.3    Hansen, H.-J.4
  • 42
    • 0042523918 scopus 로고
    • Kinetics of the Cope rearrangement of a 3,4-diphenylhexa-1,5-diene
    • doi: 10.1021/jo01307a038.
    • Lutz RP, Berg HAJ. Kinetics of the Cope rearrangement of a 3, 4-diphenylhexa-1, 5-diene. J Org Chem 1980, 45: 3915-3916. doi: 10.1021/jo01307a038.
    • (1980) J Org Chem , vol.45 , pp. 3915-3916
    • Lutz, R.P.1    Berg, H.A.J.2
  • 43
    • 0001687107 scopus 로고
    • Variable transition state structure in 3,3-sigmatropic shifts from α-secondary deuterium isotope effects
    • doi: 10.1021/ja00516a035.
    • Gajewski JJ, Conrad ND. Variable transition state structure in 3, 3-sigmatropic shifts from α-secondary deuterium isotope effects. J Am Chem Soc 1979, 101: 6693-6704. doi: 10.1021/ja00516a035.
    • (1979) J Am Chem Soc , vol.101 , pp. 6693-6704
    • Gajewski, J.J.1    Conrad, N.D.2
  • 44
    • 0000334287 scopus 로고
    • Perturbation of the degenerate, concerted Cope rearrangement by two phenyl groups in active positions of (E)-1,4-diphenylhexa-1,5-diene. Acceleration by high pressure as criterion of cyclic transition states
    • doi: 10.1021/ja00089a018.
    • Doering WvE, Birladeanu L, Sarma K, Teles JH, Klaerner FG, Gehrke J-S. Perturbation of the degenerate, concerted Cope rearrangement by two phenyl groups in active positions of (E)-1, 4-diphenylhexa-1, 5-diene. Acceleration by high pressure as criterion of cyclic transition states. J Am Chem Soc 1994, 116: 4289-4297. doi: 10.1021/ja00089a018.
    • (1994) J Am Chem Soc , vol.116 , pp. 4289-4297
    • Doering, W.1    Birladeanu, L.2    Sarma, K.3    Teles, J.H.4    Klaerner, F.G.5    Gehrke, J.-S.6
  • 47
    • 0033579184 scopus 로고    scopus 로고
    • * study of the Cope rearrangements of substituted 1,5-hexadienes provides computational evidence for a chameleonic transition state
    • doi: 10.1021/ja990476m.
    • * study of the Cope rearrangements of substituted 1, 5-hexadienes provides computational evidence for a chameleonic transition state. J Am Chem Soc 1999, 121: 10529-10537. doi: 10.1021/ja990476m.
    • (1999) J Am Chem Soc , vol.121 , pp. 10529-10537
    • Hrovat, D.A.1    Beno, B.R.2    Lange, H.3    Yoo, H.Y.4    Houk, K.N.5    Borden, W.T.6
  • 48
    • 0037133976 scopus 로고    scopus 로고
    • Theoretical analysis of the Cope rearrangement of 1,5-hexadiene and phenyl derivatives
    • doi: 10.1016/S0166-1280(01)00810-7.
    • Sakai S. Theoretical analysis of the Cope rearrangement of 1, 5-hexadiene and phenyl derivatives. J Mol Struct (THEOCHEM) 2002, 583: 181-188. doi: 10.1016/S0166-1280(01)00810-7.
    • (2002) J Mol Struct (THEOCHEM) , vol.583 , pp. 181-188
    • Sakai, S.1
  • 49
    • 27744461404 scopus 로고    scopus 로고
    • A simple mathematical model for the cooperative and competitive substitutent effects found in the Cope rearrangement of phenyl-substituted 1,5-hexadiens
    • doi: 10.1021/ct049929q.
    • Hrovat DA, Borden WT. A simple mathematical model for the cooperative and competitive substitutent effects found in the Cope rearrangement of phenyl-substituted 1, 5-hexadiens. J Chem Theory Comput 2005, 1: 87-94. doi: 10.1021/ct049929q.
    • (2005) J Chem Theory Comput , vol.1 , pp. 87-94
    • Hrovat, D.A.1    Borden, W.T.2
  • 50
    • 0033520780 scopus 로고    scopus 로고
    • Perturbation of Cope's rearrangement: 1,3,5-triphenylhexa-l,5-diene. Cham-eleonic or centauric transition region?
    • doi: 10.1021/ja9908568.
    • Doering WvE, Wang Y. Perturbation of Cope's rearrangement: 1, 3, 5-triphenylhexa-l, 5-diene. Cham-eleonic or centauric transition region? J Am Chem Soc 1999, 121: 10112-10118. doi: 10.1021/ja9908568.
    • (1999) J Am Chem Soc , vol.121 , pp. 10112-10118
    • Doering, W.1    Wang, Y.2
  • 51
    • 27744435341 scopus 로고    scopus 로고
    • A joint study based on the electron localization function and catastrophe theory of the chameleonic and centauric models for the Cope rearrangement of 1,5-hexadiene and its cyano derivatives
    • doi: 10.1002/jcc.20272.
    • Polo V, Andrés J. A joint study based on the electron localization function and catastrophe theory of the chameleonic and centauric models for the Cope rearrangement of 1, 5-hexadiene and its cyano derivatives. J Comput Chem 2005, 26: 1427-1437. doi: 10.1002/jcc.20272.
    • (2005) J Comput Chem , vol.26 , pp. 1427-1437
    • Polo, V.1    Andrés, J.2
  • 53
    • 0001568378 scopus 로고
    • The Cope rearrangement. MINDO/3 studies of the rearrangements of 1,5-hexadiene and bicyclo[2.2.0]hexane
    • doi: 10.1021/ja00457a029.
    • Dewar MJS, Ford GP, McKee ML, Rzepa HS, Wade LE. The Cope rearrangement. MINDO/3 studies of the rearrangements of 1, 5-hexadiene and bicyclo[2.2.0]hexane. J Am Chem Soc 1977, 99: 5069-5073. doi: 10.1021/ja00457a029.
    • (1977) J Am Chem Soc , vol.99 , pp. 5069-5073
    • Dewar, M.J.S.1    Ford, G.P.2    McKee, M.L.3    Rzepa, H.S.4    Wade, L.E.5
  • 54
    • 0001657212 scopus 로고
    • An AMI study of the Cope rearrangements of bullvalene, barbaralane, semibullvalene, and derivatives of semibullvalene
    • doi: 10.1016/S0040-4020(01)85913-5.
    • Dewar MJS, Jie C. An AMI study of the Cope rearrangements of bullvalene, barbaralane, semibullvalene, and derivatives of semibullvalene. Tetrahedron 1988, 44: 1351-1358. doi: 10.1016/S0040-4020(01)85913-5.
    • (1988) Tetrahedron , vol.44 , pp. 1351-1358
    • Dewar, M.J.S.1    Jie, C.2
  • 55
    • 0000238516 scopus 로고
    • Ab initio calculation of the transition state for the cope rearrangement
    • doi: 10.1021/ja00323a055.
    • Osamura Y, Kato S, Morokuma K, Feller D, Davidson ER, Borden WT. Ab initio calculation of the transition state for the cope rearrangement. J Am Chem Soc 1984, 106: 3362-3363. doi: 10.1021/ja00323a055.
    • (1984) J Am Chem Soc , vol.106 , pp. 3362-3363
    • Osamura, Y.1    Kato, S.2    Morokuma, K.3    Feller, D.4    Davidson, E.R.5    Borden, W.T.6
  • 56
    • 0034639422 scopus 로고    scopus 로고
    • Diradical character of the Cope rearrangement transition state
    • doi: 10.1021/ja993375x.
    • Staroverov VN, Davidson ER. Diradical character of the Cope rearrangement transition state. J Am Chem Soc 2000, 122: 186-187. doi: 10.1021/ja993375x.
    • (2000) J Am Chem Soc , vol.122 , pp. 186-187
    • Staroverov, V.N.1    Davidson, E.R.2
  • 57
    • 0001320706 scopus 로고
    • The Cope rearrangement revisited with multireference perturbation theory
    • doi: 10.1021/ja00107a021.
    • Kozlowski PM, Dupuis M, Davidson ER. The Cope rearrangement revisited with multireference perturbation theory. J Am Chem Soc 1995, 117: 774-778. doi: 10.1021/ja00107a021.
    • (1995) J Am Chem Soc , vol.117 , pp. 774-778
    • Kozlowski, P.M.1    Dupuis, M.2    Davidson, E.R.3
  • 58
    • 0001461906 scopus 로고
    • Density functional theory isotope effects and activation energies for the Cope and Claisen rearrangements
    • doi: 10.1021/ja00101a078.
    • Wiest O, Black KA, Houk KN. Density functional theory isotope effects and activation energies for the Cope and Claisen rearrangements. J Am Chem Soc 1994, 116: 10336-10337. doi: 10.1021/ja00101a078.
    • (1994) J Am Chem Soc , vol.116 , pp. 10336-10337
    • Wiest, O.1    Black, K.A.2    Houk, K.N.3
  • 59
    • 14744297093 scopus 로고    scopus 로고
    • Balancing dynamic and nondynamic correlation for diradical and aromatic transition states: a renormalized coupled-cluster study of the Cope rearrangement of 1,5-hexadiene
    • doi: 10.1021/ja044734d.
    • McGuire MJ, Piecuch P. Balancing dynamic and nondynamic correlation for diradical and aromatic transition states: a renormalized coupled-cluster study of the Cope rearrangement of 1, 5-hexadiene. J Am Chem Soc 2005, 127: 2608-2614. doi: 10.1021/ja044734d.
    • (2005) J Am Chem Soc , vol.127 , pp. 2608-2614
    • McGuire, M.J.1    Piecuch, P.2
  • 60
    • 33748242533 scopus 로고
    • The Cope rearrangement transition structure. Is not diradicaloid, but is it aromatic?
    • doi: 10.1002/anie.199503341.
    • Jiao H, Schleyer PvR. The Cope rearrangement transition structure. Is not diradicaloid, but is it aromatic? Angew Chem Int Ed 1995, 34: 334-337. doi: 10.1002/anie.199503341.
    • (1995) Angew Chem Int Ed , vol.34 , pp. 334-337
    • Jiao, H.1    Schleyer, P.2
  • 61
    • 37049119197 scopus 로고    scopus 로고
    • New preparation of cis-divinylcyclopropane
    • doi: 10.1039/C3975000283a.
    • Schneider MP, Rebell J. New preparation of cis-divinylcyclopropane. J Chem Soc Chem Commun 1975: 283. doi: 10.1039/C3975000283a.
    • J Chem Soc Chem Commun , vol.1975 , pp. 283
    • Schneider, M.P.1    Rebell, J.2
  • 62
    • 84982341317 scopus 로고
    • Kleine Kohlenstoff-Ringe I Über den Mechanismus der Butadien-Dimerisation zum Achtring
    • doi: 10.1002/jlac.19586150102.
    • Vogel E. Kleine Kohlenstoff-Ringe I Über den Mechanismus der Butadien-Dimerisation zum Achtring. Justus Liebigs Ann Chem 1958, 615: 1-14. doi: 10.1002/jlac.19586150102.
    • (1958) Justus Liebigs Ann Chem , vol.615 , pp. 1-14
    • Vogel, E.1
  • 63
    • 37049135527 scopus 로고
    • Isolation and characterisation of cis-divinylcyclopropane
    • doi: 10.1039/C39730000301.
    • Brown JM, Golding BT, Stofko Jun. JJ. Isolation and characterisation of cis-divinylcyclopropane. J Chem Soc Chem Commun 1973:319-320. doi: 10.1039/C39730000301.
    • (1973) J Chem Soc Chem Commun , pp. 319-320
    • Brown, J.M.1    Golding, B.T.2    Stofko Jun., J.J.3
  • 64
    • 0142010607 scopus 로고    scopus 로고
    • Transition structures and energetics for the Cope rearrangement of cis-1,2-divinylcyclopropane: an ab initio study
    • doi: 10.1016/S0166-1280(03)00478-0.
    • Zora M, Özkan I, Danisman MF. Transition structures and energetics for the Cope rearrangement of cis-1, 2-divinylcyclopropane: an ab initio study. J Mol Struct (THEOCHEM) 2003, 636: 9-13. doi: 10.1016/S0166-1280(03)00478-0.
    • (2003) J Mol Struct (THEOCHEM) , vol.636 , pp. 9-13
    • Zora, M.1    Özkan, I.2    Danisman, M.F.3
  • 65
    • 0345097548 scopus 로고    scopus 로고
    • Transition structures, energetics, and secondary kinetic isotope effects for Cope rearrangements of cis-1,2-divinylcyclobutane and cis-1,2-divinylcyclopropane: a DFT study
    • doi: 10.1021/jo035173w.
    • Ozkan I, Zora M. Transition structures, energetics, and secondary kinetic isotope effects for Cope rearrangements of cis-1, 2-divinylcyclobutane and cis-1, 2-divinylcyclopropane: a DFT study. J Org Chem 2003, 68: 9635-9642. doi: 10.1021/jo035173w.
    • (2003) J Org Chem , vol.68 , pp. 9635-9642
    • Ozkan, I.1    Zora, M.2
  • 66
    • 33845676161 scopus 로고
    • The chemistry of barrelene. III. A unique photoisomerization to semibullvalene
    • doi: 10.1021/ja00953a045.
    • Zimmerman HE, Grunewald GL. The chemistry of barrelene. III. A unique photoisomerization to semibullvalene. J Am Chem Soc 1966, 88: 183-184. doi: 10.1021/ja00953a045.
    • (1966) J Am Chem Soc , vol.88 , pp. 183-184
    • Zimmerman, H.E.1    Grunewald, G.L.2
  • 67
    • 0005972780 scopus 로고
    • The degenerate Cope rearrangement of tricyclo[3.3.1.04,6] nona-2,7-diene-9-one
    • doi: 10.1016/S0040-4039(01)90938-4.
    • Lambert JB. The degenerate Cope rearrangement of tricyclo[3.3.1.04, 6] nona-2, 7-diene-9-one. Tetrahedron Lett 1963, 4: 1901-1906. doi: 10.1016/S0040-4039(01)90938-4.
    • (1963) Tetrahedron Lett , vol.4 , pp. 1901-1906
    • Lambert, J.B.1
  • 68
    • 2742588050 scopus 로고
    • Temperature dependent nuclear magnetic resonance spectrum of octamethylsemibullvalene
    • doi: 10.1016/S0040-4039(01)98712-X.
    • Anet FAL, Schenk GE. Temperature dependent nuclear magnetic resonance spectrum of octamethylsemibullvalene. Tetrahedron Lett 1970, 11: 4237-4240. doi: 10.1016/S0040-4039(01)98712-X.
    • (1970) Tetrahedron Lett , vol.11 , pp. 4237-4240
    • Anet, F.A.L.1    Schenk, G.E.2
  • 69
    • 0008452201 scopus 로고
    • Measurement of the rate of rearrangement of bullvalene
    • doi: 10.1016/S0040-4039(01)90897-4.
    • Saunders M. Measurement of the rate of rearrangement of bullvalene. Tetrahedron Lett 1963, 4: 1699-1702. doi: 10.1016/S0040-4039(01)90897-4.
    • (1963) Tetrahedron Lett , vol.4 , pp. 1699-1702
    • Saunders, M.1
  • 70
    • 0041843036 scopus 로고
    • Spin-echo nuclear magnetic resonance studies of chemical exchange. VI. Rearrangment of bullvalene and of its silver nitrate complex1
    • doi: 10.1021/ja01096a015.
    • Allerhand A, Gutowsky HS. Spin-echo nuclear magnetic resonance studies of chemical exchange. VI. Rearrangment of bullvalene and of its silver nitrate complex1. J Am Chem Soc 1965, 87: 4092-4096. doi: 10.1021/ja01096a015.
    • (1965) J Am Chem Soc , vol.87 , pp. 4092-4096
    • Allerhand, A.1    Gutowsky, H.S.2
  • 71
    • 0000284309 scopus 로고
    • Determination of the fluxional barrier in semibullvalene by proton and carbon-13 nuclear magnetic resonance spectroscopy
    • doi: 10.1021/ja00816a037.
    • Cheng AK, Anet FAL, Mioduski J, Meinwald J. Determination of the fluxional barrier in semibullvalene by proton and carbon-13 nuclear magnetic resonance spectroscopy. J Am Chem Soc 1974, 96: 2887-2891. doi: 10.1021/ja00816a037.
    • (1974) J Am Chem Soc , vol.96 , pp. 2887-2891
    • Cheng, A.K.1    Anet, F.A.L.2    Mioduski, J.3    Meinwald, J.4
  • 73
    • 0000270011 scopus 로고
    • Activation parameters for the degenerate Cope rearrangement of barbaralane and 3,7-disubstituted barbaralanes
    • doi: 10.1021/jo00203a001.
    • Guenther H, Runsink J, Schmickler H, Schmitt P. Activation parameters for the degenerate Cope rearrangement of barbaralane and 3, 7-disubstituted barbaralanes. J Org Chem 1985, 50: 289-293. doi: 10.1021/jo00203a001.
    • (1985) J Org Chem , vol.50 , pp. 289-293
    • Guenther, H.1    Runsink, J.2    Schmickler, H.3    Schmitt, P.4
  • 74
    • 17044404247 scopus 로고    scopus 로고
    • How important is bishomoaromatic stabilization in determining the relative barrier heights for the degenerate Cope rearrangements of semibullvalene, barbaralane, bullvalene, and dihydrobullvalene?
    • doi: 10.1021/jo048268m.
    • Hrovat DA, Brown EC, Williams RV, Quast H, Borden WT. How important is bishomoaromatic stabilization in determining the relative barrier heights for the degenerate Cope rearrangements of semibullvalene, barbaralane, bullvalene, and dihydrobullvalene? J Org Chem 2005, 70: 2627-2632. doi: 10.1021/jo048268m.
    • (2005) J Org Chem , vol.70 , pp. 2627-2632
    • Hrovat, D.A.1    Brown, E.C.2    Williams, R.V.3    Quast, H.4    Borden, W.T.5
  • 75
    • 0001075237 scopus 로고
    • Homoaromaticity
    • doi: 10.1016/S0065-3160(08)60078-7.
    • Williams RV, Kurtz HA, Bethell D. Homoaromaticity. Adv Phys Org Chem 1994, 29: 273-331. doi: 10.1016/S0065-3160(08)60078-7.
    • (1994) Adv Phys Org Chem , vol.29 , pp. 273-331
    • Williams, R.V.1    Kurtz, H.A.2    Bethell, D.3
  • 76
    • 0035139026 scopus 로고    scopus 로고
    • Semibullvalenes and related molecules: ever closer approaches to neutral homoaromaticity
    • doi: 10.1002/1099-0690(200101)2001:2<227::AID-EJOC227>3.0.CO;2-Z.
    • Williams RV. Semibullvalenes and related molecules: ever closer approaches to neutral homoaromaticity. Eur J Org Chem 2001, 2001: 227-235. doi: 10.1002/1099-0690(200101)2001:2<227::AID-EJOC227>3.0.CO;2-Z.
    • (2001) Eur J Org Chem , vol.2001 , pp. 227-235
    • Williams, R.V.1
  • 77
    • 0037132605 scopus 로고    scopus 로고
    • 2v equilibrium geometries necessarily bishomoaromatic?
    • doi: 10.1021/ja027392p.
    • 2v equilibrium geometries necessarily bishomoaromatic? J Am Chem Soc 2002, 124: 14977-14982. doi: 10.1021/ja027392p.
    • (2002) J Am Chem Soc , vol.124 , pp. 14977-14982
    • Brown, E.C.1    Henze, D.K.2    Borden, W.T.3
  • 78
    • 1542591713 scopus 로고
    • Cope rearrangements in the bullvalene series
    • doi: 10.1021/ja00735a026.
    • Dewar MJS, Schoeller WW. Cope rearrangements in the bullvalene series. J Am Chem Soc 1971, 93: 1481-1482. doi: 10.1021/ja00735a026.
    • (1971) J Am Chem Soc , vol.93 , pp. 1481-1482
    • Dewar, M.J.S.1    Schoeller, W.W.2
  • 79
    • 0030834306 scopus 로고    scopus 로고
    • Annelated semibullvalenes: a theoretical study of how they 'cope' with strain
    • doi: 10.1021/ja963165.
    • Jiao H, Nagelkerke R, Kurtz HA, Williams RV, Borden WT, Schleyer PvR. Annelated semibullvalenes: a theoretical study of how they 'cope' with strain. J Am Chem Soc 1997, 119: 5921-5929. doi: 10.1021/ja963165.
    • (1997) J Am Chem Soc , vol.119 , pp. 5921-5929
    • Jiao, H.1    Nagelkerke, R.2    Kurtz, H.A.3    Williams, R.V.4    Borden, W.T.5    Schleyer, P.6
  • 80
    • 0000547830 scopus 로고
    • The quest for a neutral homoaromatic hydrocarbon. A study of pentacyclo-[7.2.1.04,11.06,9.06,10]dodeca-1,4-diene, an annelated semibullvalene derivative
    • doi: 10.1021/jo00250a045.
    • Williams RV, Kurtz HA. The quest for a neutral homoaromatic hydrocarbon. A study of pentacyclo-[7.2.1.04, 11.06, 9.06, 10]dodeca-1, 4-diene, an annelated semibullvalene derivative. J Org Chem 1988, 53: 3626-3628. doi: 10.1021/jo00250a045.
    • (1988) J Org Chem , vol.53 , pp. 3626-3628
    • Williams, R.V.1    Kurtz, H.A.2
  • 81
    • 34548263201 scopus 로고    scopus 로고
    • Selective stabilization of transition state structures for Cope rearrangements of semibullvalene and barbaralane through interactions with halogens
    • doi: 10.1021/jp0724525.
    • Wang SC, Tantillo DJ. Selective stabilization of transition state structures for Cope rearrangements of semibullvalene and barbaralane through interactions with halogens. J Phys Chem A 2007, 111: 7149-7153. doi: 10.1021/jp0724525.
    • (2007) J Phys Chem A , vol.111 , pp. 7149-7153
    • Wang, S.C.1    Tantillo, D.J.2
  • 82
    • 77953574902 scopus 로고    scopus 로고
    • Calculations predict that carbon tunneling allows the degenerate Cope rearrangement of semibullvalene to occur rapidly at cryogenic temperatures
    • doi: 10.1021/ol100879t.
    • Zhang X, Hrovat DA, Borden WT. Calculations predict that carbon tunneling allows the degenerate Cope rearrangement of semibullvalene to occur rapidly at cryogenic temperatures. Org Lett 2010, 12: 2798-2801. doi: 10.1021/ol100879t.
    • (2010) Org Lett , vol.12 , pp. 2798-2801
    • Zhang, X.1    Hrovat, D.A.2    Borden, W.T.3
  • 83
    • 84961978926 scopus 로고    scopus 로고
    • Experimental and theoretical study of stabilization of delocalized forms of semibullvalenes and barbaralanes by dipolar and polarizable solvents. Observation of a delocalized structure that is lower in free energy than the localized form
    • doi: 10.1021/jo0502089.
    • Seefelder M, Heubes M, Quast H, Edwards WD, Armantrout JR, Williams RV, Cramer CJ, Goren AC, Hrovat DA, Borden WT. Experimental and theoretical study of stabilization of delocalized forms of semibullvalenes and barbaralanes by dipolar and polarizable solvents. Observation of a delocalized structure that is lower in free energy than the localized form. J Org Chem 2005, 70: 3437-3449. doi: 10.1021/jo0502089.
    • (2005) J Org Chem , vol.70 , pp. 3437-3449
    • Seefelder, M.1    Heubes, M.2    Quast, H.3    Edwards, W.D.4    Armantrout, J.R.5    Williams, R.V.6    Cramer, C.J.7    Goren, A.C.8    Hrovat, D.A.9    Borden, W.T.10
  • 84
    • 0002981894 scopus 로고    scopus 로고
    • The effects of substituents on the degenerate Cope rearrangement of semibullvalenes and barbaralanes
    • doi 10.1002/(SICI)1099-0690(199810)1998:10<2209::AID-EJOC2209>3.0.CO;2-G and references cited therein.
    • Jackman LM, Fernandes E, Heubes M, Quast H. The effects of substituents on the degenerate Cope rearrangement of semibullvalenes and barbaralanes. Eur J Org Chem 1998, 2209-2227. doi 10.1002/(SICI)1099-0690(199810)1998:10<2209::AID-EJOC2209>3.0.CO;2-G and references cited therein.
    • (1998) Eur J Org Chem , pp. 2209-2227
    • Jackman, L.M.1    Fernandes, E.2    Heubes, M.3    Quast, H.4
  • 85
    • 0002804331 scopus 로고    scopus 로고
    • Non-concerted Cope rearrangement
    • doi: 10.1002/(SICI)1099-0690(199806)1998:6<961::AID-EJOC961>3.0.CO;2-B.
    • Roth WR, Gleiter R, Paschmann V, Hackler UE, Fritzsche G, Lange H. Non-concerted Cope rearrangement. Eur J Org Chem 1998, 961-967. doi: 10.1002/(SICI)1099-0690(199806)1998:6<961::AID-EJOC961>3.0.CO;2-B.
    • (1998) Eur J Org Chem , pp. 961-967
    • Roth, W.R.1    Gleiter, R.2    Paschmann, V.3    Hackler, U.E.4    Fritzsche, G.5    Lange, H.6
  • 86
    • 0035398428 scopus 로고    scopus 로고
    • The Bullvalene story. The conception of Bullvalene, a molecule that has no permanent structure
    • doi: 10.1021/ed078p924.
    • Ault A. The Bullvalene story. The conception of Bullvalene, a molecule that has no permanent structure. J Chem Educ 2001, 78: 924-927. doi: 10.1021/ed078p924.
    • (2001) J Chem Educ , vol.78 , pp. 924-927
    • Ault, A.1
  • 87
    • 0002549529 scopus 로고
    • Pericyclic reaction transition-states-passions and punctilios, 1935-1995
    • doi: 10.1021/ar00050a004.
    • Houk KN, Gonzalez J, Li Y. Pericyclic reaction transition-states-passions and punctilios, 1935-1995. Acc Chem Res 1995, 28: 81-90. doi: 10.1021/ar00050a004.
    • (1995) Acc Chem Res , vol.28 , pp. 81-90
    • Houk, K.N.1    Gonzalez, J.2    Li, Y.3
  • 88
    • 34548657185 scopus 로고    scopus 로고
    • The aromaticity of pericyclic reaction transition states
    • doi: 10.1021/ed084p1535.
    • Rzepa HS. The aromaticity of pericyclic reaction transition states. J Chem Educ 2007, 84: 1535-1540. doi: 10.1021/ed084p1535.
    • (2007) J Chem Educ , vol.84 , pp. 1535-1540
    • Rzepa, H.S.1
  • 90
    • 0004266297 scopus 로고
    • Hydrocarbon thermal isomerization
    • In: Wasserman HH, ed. New York: Academic Press;.
    • Gajewski JJ. Hydrocarbon thermal isomerization. In: Wasserman HH, ed. Organic Chemistry-A Series of Monographs. New York: Academic Press; 1981.
    • (1981) Organic Chemistry-A Series of Monographs
    • Gajewski, J.J.1
  • 91
    • 33745439242 scopus 로고    scopus 로고
    • Theoretical study on the aromaticity of transition states in pericyclic reactions
    • doi: 10.1021/jp0560011.
    • Sakai S. Theoretical study on the aromaticity of transition states in pericyclic reactions. J Phys Chem A 2006, 110: 6339-6344. doi: 10.1021/jp0560011.
    • (2006) J Phys Chem A , vol.110 , pp. 6339-6344
    • Sakai, S.1
  • 92
    • 11644271412 scopus 로고    scopus 로고
    • Aromaticity of pericyclic reaction transition structures: magnetic evidences
    • doi: 10.1002/(SICI)1099-1395(199808/09)11:8/9<655::AID-POC66>3.0.CO;2-U.
    • Jiao H, Schleyer PvR. Aromaticity of pericyclic reaction transition structures: magnetic evidences. J Phys Org Chem 1998, 11: 655-662. doi: 10.1002/(SICI)1099-1395(199808/09)11:8/9<655::AID-POC66>3.0.CO;2-U.
    • (1998) J Phys Org Chem , vol.11 , pp. 655-662
    • Jiao, H.1    Schleyer, P.2
  • 94
    • 33748960439 scopus 로고
    • Transition structures of hydrocarbon pericyclic reactions
    • doi: 10.1002/anie.199206821.
    • Houk KN, Li Y, Evanseck JD. Transition structures of hydrocarbon pericyclic reactions. Angew Chem Int Ed 1992, 31: 682-708. doi: 10.1002/anie.199206821.
    • (1992) Angew Chem Int Ed , vol.31 , pp. 682-708
    • Houk, K.N.1    Li, Y.2    Evanseck, J.D.3
  • 95
    • 0342713055 scopus 로고
    • Mechanistic aspects of Diels-Alder reactions: a critical survey
    • doi: 10.1002/anie.198007791.
    • Sauer J, Sustmann R. Mechanistic aspects of Diels-Alder reactions: a critical survey. Angew Chem Int Ed Eng 1980, 19: 779-807. doi: 10.1002/anie.198007791.
    • (1980) Angew Chem Int Ed Eng , vol.19 , pp. 779-807
    • Sauer, J.1    Sustmann, R.2
  • 96
    • 4344610661 scopus 로고    scopus 로고
    • Claisen rearrangement over the past nine decades
    • doi: 10.1021/cr020703u.
    • Martin Castro AM. Claisen rearrangement over the past nine decades. Chem Rev 2004, 104: 2939-3002. doi: 10.1021/cr020703u.
    • (2004) Chem Rev , vol.104 , pp. 2939-3002
    • Martin Castro, A.M.1
  • 97
    • 0001059462 scopus 로고
    • Intramolecular pericyclic reactions of acetylenic compounds
    • doi: 10.1016/S0040-4020(01)98877-5.
    • Viola A, Collins JJ, Filipp N. Intramolecular pericyclic reactions of acetylenic compounds. Tetrahedron 1981, 37: 3765-3811. doi: 10.1016/S0040-4020(01)98877-5.
    • (1981) Tetrahedron , vol.37 , pp. 3765-3811
    • Viola, A.1    Collins, J.J.2    Filipp, N.3
  • 98
    • 0001520006 scopus 로고
    • The thermal rearrangement of 1-alken-5-yncs and 1,2,5-alkatrienes
    • doi: 10.1021/ja00976a028.
    • Huntsman WD, De Boer JA, Woosley MH. The thermal rearrangement of 1-alken-5-yncs and 1, 2, 5-alkatrienes. J Am Chem Soc 1966, 88: 5846-5850. doi: 10.1021/ja00976a028.
    • (1966) J Am Chem Soc , vol.88 , pp. 5846-5850
    • Huntsman, W.D.1    De Boer, J.A.2    Woosley, M.H.3
  • 99
    • 33947335843 scopus 로고
    • The thermal rearrangement of 1,5-hexadiyne and related compounds1
    • doi: 10.1021/ja00978a030.
    • Huntsman WD, Wristers HJ. The thermal rearrangement of 1, 5-hexadiyne and related compounds1. J Am Chem Soc 1967, 89: 342-347. doi: 10.1021/ja00978a030.
    • (1967) J Am Chem Soc , vol.89 , pp. 342-347
    • Huntsman, W.D.1    Wristers, H.J.2
  • 100
    • 17344369085 scopus 로고
    • Exclusion of a 1,4-cyclohexenediyl as a metastable intermediate in the [3,3] sigmatropic rearrangement of a 1-hexen-5-yne
    • doi: 10.1021/ja00210a068.
    • Owens KA, Berson JA. Exclusion of a 1, 4-cyclohexenediyl as a metastable intermediate in the [3, 3] sigmatropic rearrangement of a 1-hexen-5-yne. J Am Chem Soc 1988, 110: 627-628. doi: 10.1021/ja00210a068.
    • (1988) J Am Chem Soc , vol.110 , pp. 627-628
    • Owens, K.A.1    Berson, J.A.2
  • 101
    • 0346598017 scopus 로고
    • Thermische Isomerisierungen, IV Die Propargyl-Cope-Umlagerung von 4-Methyl-hexadien-(1.2)-in-(5)
    • doi: 10.1016/S0040-4039(01)94102-4.
    • Hopf H. Thermische Isomerisierungen, IV Die Propargyl-Cope-Umlagerung von 4-Methyl-hexadien-(1.2)-in-(5). Tetrahedron Lett 1972, 13: 3571-3574. doi: 10.1016/S0040-4039(01)94102-4.
    • (1972) Tetrahedron Lett , vol.13 , pp. 3571-3574
    • Hopf, H.1
  • 102
    • 67349269531 scopus 로고    scopus 로고
    • Effect of electron-withdrawing group on the [3,3]-sigmatropic rearrangements of 1,5-enynes, 1,5-diynes and 1,2-diene-5-ynes: a theoretical study
    • doi: 10.1016/j.theochem.2009.02.033.
    • Xia Y, Zhou F, Li Y, Li W. Effect of electron-withdrawing group on the [3, 3]-sigmatropic rearrangements of 1, 5-enynes, 1, 5-diynes and 1, 2-diene-5-ynes: a theoretical study. J Mol Struct (THEOCHEM) 2009, 904: 69-73. doi: 10.1016/j.theochem.2009.02.033.
    • (2009) J Mol Struct (THEOCHEM) , vol.904 , pp. 69-73
    • Xia, Y.1    Zhou, F.2    Li, Y.3    Li, W.4
  • 103
    • 0343215663 scopus 로고
    • Thermally induced reactions of some novel allenes
    • doi: 10.1021/ja00948a019.
    • Skattebol L, Solomon S. Thermally induced reactions of some novel allenes. J Am Chem Soc 1965, 87: 4506-4513. doi: 10.1021/ja00948a019.
    • (1965) J Am Chem Soc , vol.87 , pp. 4506-4513
    • Skattebol, L.1    Solomon, S.2
  • 104
    • 37049134532 scopus 로고
    • The Thermal Unimolecular Isomerization of hepta-1,2,6-triene
    • doi: 10.1039/J19670000026.
    • Frey HM, Lister DH. The Thermal Unimolecular Isomerization of hepta-1, 2, 6-triene. J Chem Soc A 1967:26-27. doi: 10.1039/J19670000026.
    • (1967) J Chem Soc A , pp. 26-27
    • Frey, H.M.1    Lister, D.H.2
  • 106
    • 0000652837 scopus 로고
    • Stabilization of a putative cyclohexane-1,4-diyl intermediate elicits an antarafacial Cope rearrangement via a stepwise mechanism. Pyrolysis of (R,E)-5-methyl-1,2,6-octatriene to 4-methyl-3-methylene-1,5-heptadiene
    • doi: 10.1021/ja00081a009.
    • Wessel TE, Berson JA. Stabilization of a putative cyclohexane-1, 4-diyl intermediate elicits an antarafacial Cope rearrangement via a stepwise mechanism. Pyrolysis of (R, E)-5-methyl-1, 2, 6-octatriene to 4-methyl-3-methylene-1, 5-heptadiene. J Am Chem Soc 1994, 116: 495-505. doi: 10.1021/ja00081a009.
    • (1994) J Am Chem Soc , vol.116 , pp. 495-505
    • Wessel, T.E.1    Berson, J.A.2
  • 107
  • 108
    • 0033550518 scopus 로고    scopus 로고
    • Ab initio and DFT calculations on the Cope rearrangement of 1,2,6-heptatriene
    • doi: 10.1021/ja983032j.
    • Hrovat DA, Duncan JA, Borden WT. Ab initio and DFT calculations on the Cope rearrangement of 1, 2, 6-heptatriene. J Am Chem Soc 1999, 121: 169-175. doi: 10.1021/ja983032j.
    • (1999) J Am Chem Soc , vol.121 , pp. 169-175
    • Hrovat, D.A.1    Duncan, J.A.2    Borden, W.T.3
  • 109
    • 84985741751 scopus 로고
    • Propargyl-Stabilisierungsenergie
    • doi: 10.1002/cber.19941270930.
    • Roth WR, Hopf H, Horn C. Propargyl-Stabilisierungsenergie. Chem Ber 1994, 127: 1765-1779. doi: 10.1002/cber.19941270930.
    • (1994) Chem Ber , vol.127 , pp. 1765-1779
    • Roth, W.R.1    Hopf, H.2    Horn, C.3
  • 110
    • 0035887050 scopus 로고    scopus 로고
    • The cyclization of parent and cyclic hexa-1,3-dien-5-ynes-a combined theoretical and experimental study
    • doi: 10.1002/1521-3765(20011015)7:20<4386::AID-CHEM4386>3.0.CO;2-S.
    • Prall M, Krüger A, Schreiner PR, Hopf H. The cyclization of parent and cyclic hexa-1, 3-dien-5-ynes-a combined theoretical and experimental study. Chem Eur J 2001, 7: 4386-4394. doi: 10.1002/1521-3765(20011015)7:20<4386::AID-CHEM4386>3.0.CO;2-S.
    • (2001) Chem Eur J , vol.7 , pp. 4386-4394
    • Prall, M.1    Krüger, A.2    Schreiner, P.R.3    Hopf, H.4
  • 111
    • 33947088453 scopus 로고
    • p-Benzyne. Generation as an intermediate in a thermal isomerization reaction and trapping evidence for the 1,4-benzenediyl structure
    • doi: 10.1021/ja00757a071.
    • Jones RR, Bergman RG. p-Benzyne. Generation as an intermediate in a thermal isomerization reaction and trapping evidence for the 1, 4-benzenediyl structure. J Am Chem Soc 1972, 94: 660-661. doi: 10.1021/ja00757a071.
    • (1972) J Am Chem Soc , vol.94 , pp. 660-661
    • Jones, R.R.1    Bergman, R.G.2
  • 112
    • 0345614235 scopus 로고
    • Studies on the thermal generation and reactivity of a class of (σ-1,4-biradicals
    • doi: 10.1021/ja00050a017.
    • Myers AG, Dragovich PS, Kuo EY. Studies on the thermal generation and reactivity of a class of (σ-1, 4-biradicals. J Am Chem Soc 1992, 114: 9369-9386. doi: 10.1021/ja00050a017.
    • (1992) J Am Chem Soc , vol.114 , pp. 9369-9386
    • Myers, A.G.1    Dragovich, P.S.2    Kuo, E.Y.3
  • 113
    • 0024343657 scopus 로고
    • Biradical formation from acyclic conjugated eneyne-allene system related to neocarzinostatin and esperamicin-calichemicin
    • doi: 10.1016/S0040-4039(01)80564-5.
    • Nagata R, Yamanaka H, Okazaki E, Saito I. Biradical formation from acyclic conjugated eneyne-allene system related to neocarzinostatin and esperamicin-calichemicin. Tetrahedron Lett 1989, 30: 4995-4998. doi: 10.1016/S0040-4039(01)80564-5.
    • (1989) Tetrahedron Lett , vol.30 , pp. 4995-4998
    • Nagata, R.1    Yamanaka, H.2    Okazaki, E.3    Saito, I.4
  • 114
    • 77749289370 scopus 로고    scopus 로고
    • CASSCF molecular orbital calculations reveal a purely pseudopericyclic mechanism for a [3,3] sigmatropic rearrangement
    • Forte L, Lafortune MC, Bierzynski IR, Duncan JA. CASSCF molecular orbital calculations reveal a purely pseudopericyclic mechanism for a [3, 3] sigmatropic rearrangement. J Am Chem Soc. 132: 2196-2201.
    • J Am Chem Soc , vol.132 , pp. 2196-2201
    • Forte, L.1    Lafortune, M.C.2    Bierzynski, I.R.3    Duncan, J.A.4
  • 115
    • 15044349982 scopus 로고    scopus 로고
    • Ellipticity: a convenient tool to characterize electrocyclic reactions
    • doi: 10.1002/chem.200401026.
    • López CS, Faza ON, Cossío FP, York DM, de Lera AR. Ellipticity: a convenient tool to characterize electrocyclic reactions. Chem Eur J 2005, 11: 1734-1738. doi: 10.1002/chem.200401026.
    • (2005) Chem Eur J , vol.11 , pp. 1734-1738
    • López, C.S.1    Faza, O.N.2    Cossío, F.P.3    York, D.M.4    de Lera, A.R.5
  • 116
    • 18744368176 scopus 로고    scopus 로고
    • Are electrocyclization reactions of (3Z)-1,3,5-hexatrienone and nitrogen derivatives pseudopericyclic? A DFT study
    • doi: 10.1021/j00477695.
    • Cabaleiro-Lago EM, Rodríguez-Otero J, Varela-Varela SM, Peña-Gallego A, Hermida-Ramon JM. Are electrocyclization reactions of (3Z)-1, 3, 5-hexatrienone and nitrogen derivatives pseudopericyclic? A DFT study. J Org Chem 2005, 70: 3921-3928. doi: 10.1021/j00477695.
    • (2005) J Org Chem , vol.70 , pp. 3921-3928
    • Cabaleiro-Lago, E.M.1    Rodríguez-Otero, J.2    Varela-Varela, S.M.3    Peña-Gallego, A.4    Hermida-Ramon, J.M.5
  • 117
    • 33744921882 scopus 로고    scopus 로고
    • Stepwise Cope rearrangement of cyclo-biphenalenyl via an unusual multicenter covalent π-bonded intermediate
    • doi: 10.1021/ja060427r.
    • Huang J, Kertesz M. Stepwise Cope rearrangement of cyclo-biphenalenyl via an unusual multicenter covalent π-bonded intermediate. J Am Chem Soc 2006, 128: 7277-7286. doi: 10.1021/ja060427r.
    • (2006) J Am Chem Soc , vol.128 , pp. 7277-7286
    • Huang, J.1    Kertesz, M.2
  • 118
    • 0038980242 scopus 로고    scopus 로고
    • Study of the electrocyclization of (Z)-hexa-1,3,5-triene and its heterosubstituted analogues based on ab initio and DFT calculations
    • doi: 10.1021/jo990881w.
    • Rodríguez-Otero J. Study of the electrocyclization of (Z)-hexa-1, 3, 5-triene and its heterosubstituted analogues based on ab initio and DFT calculations. J Org Chem 1999, 64: 6842-6848. doi: 10.1021/jo990881w.
    • (1999) J Org Chem , vol.64 , pp. 6842-6848
    • Rodríguez-Otero, J.1
  • 119
    • 0037006845 scopus 로고    scopus 로고
    • Electrocyclization of (Z)-1,2,4,6-heptatetraene and its heterosubstituted analogues: pericyclic or pseudopericyclic?
    • doi: 10.1002/1521-3773(20020402)41:7<1147::AID-ANIE1147>3.0.CO;2-J.
    • Rodríguez-Otero J, Cabaleiro-Lago EM. Electrocyclization of (Z)-1, 2, 4, 6-heptatetraene and its heterosubstituted analogues: pericyclic or pseudopericyclic? Angew Chem Int Ed 2002, 41: 1147-1150. doi: 10.1002/1521-3773(20020402)41:7<1147::AID-ANIE1147>3.0.CO;2-J.
    • (2002) Angew Chem Int Ed , vol.41 , pp. 1147-1150
    • Rodríguez-Otero, J.1    Cabaleiro-Lago, E.M.2
  • 120
    • 0032125865 scopus 로고    scopus 로고
    • Bergman, aza-Bergman, and protonated aza-Bergman cyclizations and intermediate 2,5-arynes: chemistry and challenges to computation
    • doi: 10.1021/ja9806579.
    • Cramer CJ. Bergman, aza-Bergman, and protonated aza-Bergman cyclizations and intermediate 2, 5-arynes: chemistry and challenges to computation. J Am Chem Soc 1998, 120: 6261-6269. doi: 10.1021/ja9806579.
    • (1998) J Am Chem Soc , vol.120 , pp. 6261-6269
    • Cramer, C.J.1
  • 121
    • 0000974225 scopus 로고    scopus 로고
    • Cycloaromatization of 1,4-pentadiynes: a viable possibility?
    • doi: 10.1021/ol0266424.
    • Kawatkar SP, Schreiner PR. Cycloaromatization of 1, 4-pentadiynes: a viable possibility? Org Lett 2002, 4: 3643-3646. doi: 10.1021/ol0266424.
    • (2002) Org Lett , vol.4 , pp. 3643-3646
    • Kawatkar, S.P.1    Schreiner, P.R.2
  • 122
    • 0347052792 scopus 로고    scopus 로고
    • Beyond Schmittel and Myers-Saito cyclizations: rearrangements of 4-heteroatom-1,2-hexa-diene-5-ynes
    • doi: 10.1021/ol0360243.
    • Schreiner PR, Bui BH. Beyond Schmittel and Myers-Saito cyclizations: rearrangements of 4-heteroatom-1, 2-hexa-diene-5-ynes. Org Lett 2003, 5: 4871-4874. doi: 10.1021/ol0360243.
    • (2003) Org Lett , vol.5 , pp. 4871-4874
    • Schreiner, P.R.1    Bui, B.H.2
  • 123
    • 33644749232 scopus 로고    scopus 로고
    • Moore cyclizations: rearrangements of 3-heteroatom-pent-1-en-4-yn-1-ones-a computational search for new reactions
    • doi: 10.1002/ejoc.200500776.
    • Schreiner PR, Bui BH. Moore cyclizations: rearrangements of 3-heteroatom-pent-1-en-4-yn-1-ones-a computational search for new reactions. Eur J Org Chem 2006: 1162-1165. doi: 10.1002/ejoc.200500776.
    • Eur J Org Chem , vol.2006 , pp. 1162-1165
    • Schreiner, P.R.1    Bui, B.H.2
  • 124
    • 77951601858 scopus 로고    scopus 로고
    • Heuristic thinking makes a chemist smart
    • doi: 10.1039/b911536f.
    • Graulich N, Hopf H, Schreiner PR. Heuristic thinking makes a chemist smart. Chem Soc Rev 2010, 39: 1503-1512. doi: 10.1039/b911536f.
    • (2010) Chem Soc Rev , vol.39 , pp. 1503-1512
    • Graulich, N.1    Hopf, H.2    Schreiner, P.R.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.