메뉴 건너뛰기




Volumn 32, Issue 9, 1999, Pages 815-824

Photoinduced electron-transfer intramolecular cyclization of acyclic dienes with two styrene units

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; ALKENE; BICYCLO COMPOUND; CYCLOHEXANE DERIVATIVE; STYRENE;

EID: 0032856679     PISSN: 00014842     EISSN: None     Source Type: Journal    
DOI: 10.1021/ar960002h     Document Type: Article
Times cited : (30)

References (71)
  • 1
    • 33845375409 scopus 로고
    • Photochemical electron-transfer reactions of 1,1-diarylethylenes
    • Mattes, S. L.; Farid, S. Photochemical Electron-Transfer Reactions of 1,1-Diarylethylenes. J. Am. Chem. Soc. 1986, 108, 7356-7361. Tojo, S.; Toki, S.; Takamuku, S. Acyclic 1,4-Radical Cations. Direct Observation and Stability. J. Org. Chem. 1991, 56, 6240-6243. Tojo, S.; Toki, S.; Takamuku, S. Formation and Reactivity of Dimer Radical Cations of 4-Methoxystyrene. Radiat. Phys. Chem. 1992, 40, 95-99. Brede, O.; David, F.; Steenken, S. Photo- and Radiation-Induced Chemical Generation and Reaction of Styrene Radical Cation in Polar and Non-Polar Solvents. J. Chem. Soc., Perkin Trans. 2 1995, 23-32.
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 7356-7361
    • Mattes, S.L.1    Farid, S.2
  • 2
    • 0000718238 scopus 로고
    • Acyclic 1,4-radical cations. Direct observation and stability
    • Mattes, S. L.; Farid, S. Photochemical Electron-Transfer Reactions of 1,1-Diarylethylenes. J. Am. Chem. Soc. 1986, 108, 7356-7361. Tojo, S.; Toki, S.; Takamuku, S. Acyclic 1,4-Radical Cations. Direct Observation and Stability. J. Org. Chem. 1991, 56, 6240-6243. Tojo, S.; Toki, S.; Takamuku, S. Formation and Reactivity of Dimer Radical Cations of 4-Methoxystyrene. Radiat. Phys. Chem. 1992, 40, 95-99. Brede, O.; David, F.; Steenken, S. Photo- and Radiation-Induced Chemical Generation and Reaction of Styrene Radical Cation in Polar and Non-Polar Solvents. J. Chem. Soc., Perkin Trans. 2 1995, 23-32.
    • (1991) J. Org. Chem. , vol.56 , pp. 6240-6243
    • Tojo, S.1    Toki, S.2    Takamuku, S.3
  • 3
    • 0026910973 scopus 로고
    • Formation and reactivity of dimer radical cations of 4-methoxystyrene
    • Mattes, S. L.; Farid, S. Photochemical Electron-Transfer Reactions of 1,1-Diarylethylenes. J. Am. Chem. Soc. 1986, 108, 7356-7361. Tojo, S.; Toki, S.; Takamuku, S. Acyclic 1,4-Radical Cations. Direct Observation and Stability. J. Org. Chem. 1991, 56, 6240-6243. Tojo, S.; Toki, S.; Takamuku, S. Formation and Reactivity of Dimer Radical Cations of 4-Methoxystyrene. Radiat. Phys. Chem. 1992, 40, 95-99. Brede, O.; David, F.; Steenken, S. Photo- and Radiation-Induced Chemical Generation and Reaction of Styrene Radical Cation in Polar and Non-Polar Solvents. J. Chem. Soc., Perkin Trans. 2 1995, 23-32.
    • (1992) Radiat. Phys. Chem. , vol.40 , pp. 95-99
    • Tojo, S.1    Toki, S.2    Takamuku, S.3
  • 4
    • 37049071861 scopus 로고
    • Photo- and radiation-induced chemical generation and reaction of styrene radical cation in polar and non-polar solvents
    • Mattes, S. L.; Farid, S. Photochemical Electron-Transfer Reactions of 1,1-Diarylethylenes. J. Am. Chem. Soc. 1986, 108, 7356-7361. Tojo, S.; Toki, S.; Takamuku, S. Acyclic 1,4-Radical Cations. Direct Observation and Stability. J. Org. Chem. 1991, 56, 6240-6243. Tojo, S.; Toki, S.; Takamuku, S. Formation and Reactivity of Dimer Radical Cations of 4-Methoxystyrene. Radiat. Phys. Chem. 1992, 40, 95-99. Brede, O.; David, F.; Steenken, S. Photo- and Radiation-Induced Chemical Generation and Reaction of Styrene Radical Cation in Polar and Non-Polar Solvents. J. Chem. Soc., Perkin Trans. 2 1995, 23-32.
    • (1995) J. Chem. Soc., Perkin Trans. 2 , pp. 23-32
    • Brede, O.1    David, F.2    Steenken, S.3
  • 6
    • 0000410853 scopus 로고
    • Contact and solvent-separated radical ion pairs in organic photochemistry
    • Mattay, J., Ed.; Springer-Verlag: Berlin
    • (b) Mattay, J.; Vondenhof, M. Contact and Solvent-Separated Radical Ion pairs in Organic Photochemistry. In Topics in Current Chemistry: Photoinduced Electron Transfer III; Mattay, J., Ed.; Springer-Verlag: Berlin, 1990; Vol. 159, pp 219-255.
    • (1990) Topics in Current Chemistry: Photoinduced Electron Transfer III , vol.159 , pp. 219-255
    • Mattay, J.1    Vondenhof, M.2
  • 7
    • 0000015083 scopus 로고
    • Structure and reactivity of organic radical cations
    • Mattay, J., Ed.; Springer-Verlag: Berlin
    • (c) Roth, H. D. Structure and Reactivity of Organic Radical Cations. In Topics in Current Chemistry: Photoinduced Electron Transfer IV; Mattay, ]., Ed.; Springer-Verlag: Berlin, 1992; Vol. 163, pp 131-245.
    • (1992) Topics in Current Chemistry: Photoinduced Electron Transfer IV , vol.163 , pp. 131-245
    • Roth, H.D.1
  • 8
    • 0004720754 scopus 로고    scopus 로고
    • Kinetics and mechanisms for the reactions of alkene radical cations
    • Mariano, P. S., Ed.; JAI: London
    • (d) Johnston, L. J.; Schepp, N. P. Kinetics and Mechanisms for the Reactions of Alkene Radical Cations. In Advances in Electron Transfer Chemistry, Mariano, P. S., Ed.; JAI: London, 1996; Vol. 5, pp 41-102.
    • (1996) Advances in Electron Transfer Chemistry , vol.5 , pp. 41-102
    • Johnston, L.J.1    Schepp, N.P.2
  • 9
    • 0000203357 scopus 로고
    • Kinetics of the cope rearrangement of 1,1-dideuteriohexa-1,5-diene
    • (a) Doering, W. v. E.; Toscano, V. G.; Beasley, G. H. Kinetics of the Cope Rearrangement of 1,1-Dideuteriohexa-1,5-diene. Tetrahedron 1971, 27, 5299-5306.
    • (1971) Tetrahedron , vol.27 , pp. 5299-5306
    • Doering, W.V.E.1    Toscano, V.G.2    Beasley, G.H.3
  • 10
    • 0025374692 scopus 로고
    • "Frustrated" cope rearrangement: Thermal inter-conversion of 2,6-diphenylhepta-1,6-diene and 1,5-diphenylbicyclo[3.2.0]heptane
    • (b) Roth, W. R.; Lennarts, H.-W.; Doering, W. v. E.; Birladeanu, L.; Guyton, C. A.; Kitagawa, T. A "Frustrated" Cope Rearrangement: Thermal Inter-conversion of 2,6-Diphenylhepta-1,6-diene and 1,5-Diphenylbicyclo[3.2.0]heptane. J. Am. Chem. Soc. 1990, 112, 1722-1732.
    • (1990) J. Am. Chem. Soc. , vol.112 , pp. 1722-1732
    • Roth, W.R.1    Lennarts, H.-W.2    Doering, W.V.E.3    Birladeanu, L.4    Guyton, C.A.5    Kitagawa, T.A.6
  • 11
    • 0001739127 scopus 로고
    • The possible role of 1,4-cyclohexylene intermediates in cope rearrangements
    • (a) Dewar, M. J. S.; Wade, L. E. The Possible Role of 1,4-Cyclohexylene Intermediates in Cope Rearrangements. J. Am. Chem. Soc. 1973, 95, 290-291.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 290-291
    • Dewar, M.J.S.1    Wade, L.E.2
  • 12
    • 0001036539 scopus 로고
    • A study of the mechanism of the cope rearrangement
    • (b) Dewar, M. J. S.; Wade, L. E., Jr. A Study of the Mechanism of the Cope Rearrangement. J. Am. Chem. Soc. 1977, 99, 4417-4424.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 4417-4424
    • Dewar, M.J.S.1    Wade L.E., Jr.2
  • 13
    • 0001568378 scopus 로고
    • The cope rearrangement. MINDO/3 studies of the rearrangements of the 1,5-hexadiene and bicyclo[2.2.0]hexane
    • (c) Dewar, M. J. S.; Ford, G. P.; McKee, M. L.; Rzepa, H. S.; Wade, L. E. The Cope Rearrangement. MINDO/3 Studies of the Rearrangements of the 1,5-Hexadiene and Bicyclo[2.2.0]hexane, J. Am. Chem. Soc. 1977, 99, 5069-5073.
    • (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
  • 14
    • 0021169192 scopus 로고
    • Multibond reactions cannot normally be synchronous
    • (d) Dewar, M. J. S. Multibond Reactions Cannot Normally Be Synchronous. J. Am. Chem. Soc. 1984, 106, 209-219.
    • (1984) J. Am. Chem. Soc. , vol.106 , pp. 209-219
    • Dewar, M.J.S.1
  • 15
    • 0000708426 scopus 로고
    • Mechanism of the cope rearrangement
    • (e) Dewar, M. J. S.; Jie, C. Mechanism of the Cope Rearrangement. J. Am. Chem. Soc. 1987, 109, 5893-5900.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 5893-5900
    • Dewar, M.J.S.1    Jie, C.2
  • 16
    • 0001347948 scopus 로고
    • Mechanisms of pericyclic reactions: The role of quantitative theory in the study of reaction mechanisms
    • (f) Dewar, M. J. S.; Jie, C. Mechanisms of Pericyclic Reactions: The Role of Quantitative Theory in the Study of Reaction Mechanisms. Acc. Chem. Res. 1992, 25, 537-543.
    • (1992) Acc. Chem. Res. , vol.25 , pp. 537-543
    • Dewar, M.J.S.1    Jie, C.2
  • 17
    • 0039917775 scopus 로고
    • Variable transition-state structure in the cope rearrangement as deduced from secondary deuterium kinetic isotope effects
    • (a) Gajewski, J. J.; Conrad, N. D. Variable Transition-State Structure in the Cope Rearrangement as Deduced from Secondary Deuterium Kinetic Isotope Effects. J. Am. Chem. Soc. 1978, 100, 6269-6270.
    • (1978) J. Am. Chem. Soc. , vol.100 , pp. 6269-6270
    • Gajewski, J.J.1    Conrad, N.D.2
  • 18
    • 0001687107 scopus 로고
    • Variable transition state structure in 3,3-sigmatropic shifts from α-secondary deuterium isotope effects
    • (b) Gajewski, J. J.; Conrad, N. D. Variable Transition State Structure in 3,3-Sigmatropic Shifts from α-Secondary Deuterium Isotope Effects. J. Am. Chem. Soc. 1979, 101, 6693-6704.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 6693-6704
    • Gajewski, J.J.1    Conrad, N.D.2
  • 19
    • 0000052365 scopus 로고
    • Energy surfaces of sigmatropic shifts
    • (c) Gajewski, J. J. Energy Surfaces of Sigmatropic Shifts. Acc. Chem. Res. 1980, 13, 142-148.
    • (1980) Acc. Chem. Res. , vol.13 , pp. 142-148
    • Gajewski, J.J.1
  • 21
    • 0000926935 scopus 로고    scopus 로고
    • A new class of non-kekulé molecules with tunable singlet-triplet energy spacings
    • (a) Berson, J. A. A New Class of Non-Kekulé Molecules with Tunable Singlet-Triplet Energy Spacings. Acc. Chem. Res. 1997, 30, 238-244.
    • (1997) Acc. Chem. Res. , vol.30 , pp. 238-244
    • Berson, J.A.1
  • 22
    • 0000456381 scopus 로고
    • Heterocyclic aromatic non-kekulé molecules. Synthesis and solution-phase chemistry of the singlet biradicals 3,4-dimethylenefuran and 3,4-dimethylenethiophene
    • (b) Stone, K. J.; Greenberg, M. M.; Blackstock, S. C.; Berson, J. A. Heterocyclic Aromatic Non-Kekulé Molecules. Synthesis and Solution-Phase Chemistry of the Singlet Biradicals 3,4-Dimethylenefuran and 3,4-Dimethylenethiophene. J. Am. Chem. Soc. 1989, 111, 3659-3671.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 3659-3671
    • Stone, K.J.1    Greenberg, M.M.2    Blackstock, S.C.3    Berson, J.A.4
  • 23
    • 0012144955 scopus 로고
    • Ground-state multiplicities of 3,4-dimethylenefuran and 3,4-dimethylenethiophene. Experimental tests of ab initio and semiempirical theories of heteroatom-bridged disjoint biradicals
    • (c) Greenberg, M. M.; Blackstock, S. C.; Stone, K. J.; Berson, J. A. Ground-State Multiplicities of 3,4-Dimethylenefuran and 3,4-Dimethylenethiophene. Experimental Tests of ab Initio and Semiempirical Theories of Heteroatom-Bridged Disjoint Biradicals. J. Am. Chem. Soc. 1989, 111, 3671-3679.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 3671-3679
    • Greenberg, M.M.1    Blackstock, S.C.2    Stone, K.J.3    Berson, J.A.4
  • 24
    • 0030896462 scopus 로고    scopus 로고
    • Tuning the singlet-triplet energy gap in a non-kekulé series by designed structural variation. The singlet states of N-substituted-3,4-dimethylenepyrrole biradicals
    • (d) Bush, L C.; Heath, R. B.; Freg, X. W.; Wang, P. A.; Maksimovic, L; Song, A. I.; Chung, W.-S.; Berinstain, A. B.; Scaiano, J. C.; Betson, J. A. Tuning the Singlet-Triplet Energy Gap in a Non-Kekulé Series by Designed Structural Variation. The Singlet States of N-Substituted-3,4-dimethylenepyrrole Biradicals. J. Am. Chem. Soc. 1997, 119, 1406-1415.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 1406-1415
    • Bush, L.C.1    Heath, R.B.2    Freg, X.W.3    Wang, P.A.4    Maksimovic, L.5    Song, A.I.6    Chung, W.-S.7    Berinstain, A.B.8    Scaiano, J.C.9    Betson, J.A.10
  • 25
    • 0030895105 scopus 로고    scopus 로고
    • Triplet species from dihydropyrrolo[3,4-d]pyridazines; the diazene precursors of N-arenesulfonyl-3,4-dimethylenepyrroles
    • (e) Bush, L. C.; Maksimovic, L.; Freg, X. W.; Lu, H. S. M.; Berson, J. A. Triplet Species from Dihydropyrrolo[3,4-d]pyridazines; the Diazene Precursors of N-Arenesulfonyl-3,4-dimethylenepyrroles. J. Am. Chem. Soc. 1997, 119, 1416-1427.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 1416-1427
    • Bush, L.C.1    Maksimovic, L.2    Freg, X.W.3    Lu, H.S.M.4    Berson, J.A.5
  • 27
    • 0032515424 scopus 로고    scopus 로고
    • Photoinduced electron-transfer degenerate cope rearrangement of 2,5-diaryl-1,5-hexadienes: A cation radical cyclization-diradical cleavage mechanism
    • (a) Ikeda, H.; Minegishi, T.; Abe, H.; Konno, A.; Goodman, J. L.; Miyashi, T. Photoinduced Electron-Transfer Degenerate Cope Rearrangement of 2,5-Diaryl-1,5-hexadienes: A Cation Radical Cyclization-Diradical Cleavage Mechanism. J. Am. Chem. Soc. 1998, 120, 87-95.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 87-95
    • Ikeda, H.1    Minegishi, T.2    Abe, H.3    Konno, A.4    Goodman, J.L.5    Miyashi, T.6
  • 28
    • 33845279361 scopus 로고
    • Evidence for a chair cyclohexane 1,4-radical cation intermediate in the single electron transfer induced cope rearrangement of 2,5-diaryl-1,5-hexadienes
    • (b) Miyashi, T.; Konno, A.; Takahashi, Y. Evidence for a Chair Cyclohexane 1,4-Radical Cation Intermediate in the Single Electron Transfer Induced Cope Rearrangement of 2,5-Diaryl-1,5-hexadienes. J. Am. Chem. Soc. 1988, 110, 3676-3677.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 3676-3677
    • Miyashi, T.1    Konno, A.2    Takahashi, Y.3
  • 29
    • 0000587680 scopus 로고
    • Photoinduced electron-transfer reactions of the cope and related systems
    • (c) Miyashi, T.; Ikeda, H.; Konno, A.; Okitsu, O.; Takahashi, Y. Photoinduced Electron-Transfer Reactions of the Cope and Related Systems. Pure Appl. Chem. 1990, 62, 1531-1538.
    • (1990) Pure Appl. Chem. , vol.62 , pp. 1531-1538
    • Miyashi, T.1    Ikeda, H.2    Konno, A.3    Okitsu, O.4    Takahashi, Y.5
  • 30
    • 37049088139 scopus 로고
    • Striking contrast between photoinduced and non-photoinduced electron-transfer reactions of 1,4-diphenyl-2,3-diazabicyclo[2.2.2]oct-2-ene
    • (d) Ikeda, H.; Minegishi, T.; Miyashi, T. Striking Contrast between Photoinduced and Non-Photoinduced Electron-Transfer Reactions of 1,4-Diphenyl-2,3-diazabicyclo[2.2.2]oct-2-ene. J. Chem. Soc., Chem. Commun. 1994, 297-298.
    • (1994) J. Chem. Soc., Chem. Commun. , pp. 297-298
    • Ikeda, H.1    Minegishi, T.2    Miyashi, T.3
  • 31
    • 0344442594 scopus 로고    scopus 로고
    • note
    • For other studies related to the cation radical Cope rearrangement of acyclic 1,5-hexadienes, see refs 10 and 11 (experimental) and 12 (theoretical).
  • 32
    • 0010668919 scopus 로고
    • A photoassisted hole-catalyzed cope reaction on zeolite
    • (a) Lorenz, K.; Bauld, N. L. A Photoassisted Hole-Catalyzed Cope Reaction on Zeolite. J. Catal. 1985, 95, 613-616.
    • (1985) J. Catal. , vol.95 , pp. 613-616
    • Lorenz, K.1    Bauld, N.L.2
  • 33
    • 37049088697 scopus 로고
    • IV-catalysed denitrogenation of the azoalkane 1,4-diphenyl-2,3-diazabicyclo[2.2.2]oct-2-ene and its reluctance to undergo cope rearrangement
    • IV-Catalysed Denitrogenation of the Azoalkane 1,4-Diphenyl-2,3-diazabicyclo[2.2.2]oct-2-ene and Its Reluctance to Undergo Cope Rearrangement. J. Chem. Soc., Chem. Commun. 1988, 142-143.
    • (1988) J. Chem. Soc., Chem. Commun. , pp. 142-143
    • Adam, W.1    Grabowski, S.2    Miranda, M.A.3    Rübenacker, M.4
  • 34
    • 0039970050 scopus 로고
    • The cation-radical cope rearrangement of 2,5-diphenylhexa-1,5-dienes under electron ionization
    • (c) Ikeda, H.; Takasaki, T.; Takahashi, Y.; Miyashi, T. The Cation-Radical Cope Rearrangement of 2,5-Diphenylhexa-1,5-dienes under Electron Ionization. J. Chem. Soc., Chem. Commun. 1993, 367-369.
    • (1993) J. Chem. Soc., Chem. Commun. , pp. 367-369
    • Ikeda, H.1    Takasaki, T.2    Takahashi, Y.3    Miyashi, T.4
  • 35
    • 0001435443 scopus 로고
    • Azoalkanes as electron donors in charge-transfer complexes. Molecular structures with sacrificial (π*,ο*) and increvalent (v) electron acceptors
    • (a) Blackstock, S. C.; Kochi, J. K. Azoalkanes as Electron Donors in Charge-Transfer Complexes. Molecular Structures with Sacrificial (π*,ο*) and Increvalent (v) Electron Acceptors. J. Am. Chem. Soc. 1987, 109, 2484-2496.
    • (1987) J. Am. Chem. Soc. , vol.109 , pp. 2484-2496
    • Blackstock, S.C.1    Kochi, J.K.2
  • 36
    • 0000644074 scopus 로고
    • Radical cation cyclization of 1,5-hexadiene to cyclohexene via the cyclohexane-2,5-diyl radical cation intermediates
    • (b) Guo, Q.-X.; Qin, X.-Z.; Wang, J. T.; Williams, F. Radical Cation Cyclization of 1,5-hexadiene to Cyclohexene via the Cyclohexane-2,5-diyl Radical Cation Intermediates. J. Am. Chem. Soc. 1988, 110, 1974-1976.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1974-1976
    • Guo, Q.-X.1    Qin, X.-Z.2    Wang, J.T.3    Williams, F.4
  • 37
    • 33845279140 scopus 로고
    • ESR study of the 2,3-diazabicyclo[2.2.2]oct-2-ene radical cation in freon matrices
    • (c) Williams, F.; Guo, Q.-X.; Petillo, P. A.; Nelsen, S. F. ESR Study of the 2,3-Diazabicyclo[2.2.2]oct-2-ene Radical Cation in Freon Matrices. J. Am. Chem. Soc. 1988, 110, 7887-7888.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 7887-7888
    • Williams, F.1    Guo, Q.-X.2    Petillo, P.A.3    Nelsen, S.F.4
  • 38
    • 0000727174 scopus 로고
    • ESR evidence for the stereospecific formation of the chair cyclohexane-1,4-diyl radical cation from both bicyclo[2.2.0]hexane and 1,5-hexadiene
    • (d) Williams, F.; Guo, Q.-X.; Bebout, D. C.; Carpenter, B. K. ESR Evidence for the Stereospecific Formation of the Chair Cyclohexane-1,4-diyl Radical Cation from Both Bicyclo[2.2.0]hexane and 1,5-hexadiene. J. Am. Chem. Soc. 1989, 111, 4133-4134.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 4133-4134
    • Williams, F.1    Guo, Q.-X.2    Bebout, D.C.3    Carpenter, B.K.4
  • 39
    • 0000425392 scopus 로고
    • Inverted potential-energy surfaces in the radical-cation cope rearrangements of hexa-1,5-diene and semibullbalene
    • (e) Williams, F. Inverted Potential-Energy Surfaces in the Radical-Cation Cope Rearrangements of Hexa-1,5-diene and Semibullbalene. J. Chem. Soc., Faraday Trans. 1994, 90, 1681-1687.
    • (1994) J. Chem. Soc., Faraday Trans. , vol.90 , pp. 1681-1687
    • Williams, F.1
  • 40
    • 0020736210 scopus 로고
    • Theory of cation-radical pericyclic reactions
    • Bauld, N. L.; Bellville, D. J.; Pabon, P.; Chelsky, R.; Green, G. Theory of Cation-Radical Pericyclic Reactions. J. Am. Chem. Soc. 1983, 705, 2378-2382. Dunkin, I. R.; Andrews, L. Orbital Symmetry Conservation and Frontier Orbital Control in the Reactions of Organic Radical Cations. Tetrahedron 1985, 41, 145-161.
    • (1983) J. Am. Chem. Soc. , vol.705 , pp. 2378-2382
    • Bauld, N.L.1    Bellville, D.J.2    Pabon, P.3    Chelsky, R.4    Green, G.5
  • 41
    • 0001531929 scopus 로고
    • Orbital symmetry conservation and frontier orbital control in the reactions of organic radical cations
    • Bauld, N. L.; Bellville, D. J.; Pabon, P.; Chelsky, R.; Green, G. Theory of Cation-Radical Pericyclic Reactions. J. Am. Chem. Soc. 1983, 705, 2378-2382. Dunkin, I. R.; Andrews, L. Orbital Symmetry Conservation and Frontier Orbital Control in the Reactions of Organic Radical Cations. Tetrahedron 1985, 41, 145-161.
    • (1985) Tetrahedron , vol.41 , pp. 145-161
    • Dunkin, I.R.1    Andrews, L.2
  • 42
    • 0345305600 scopus 로고    scopus 로고
    • For recent reviews, see refs 2a,c and 14
    • For recent reviews, see refs 2a,c and 14.
  • 43
    • 0001446764 scopus 로고
    • Photoinduced electron transfer oxygenations
    • Mattay, J., Ed.; Springer-Verlag: Berlin
    • Lopez, L. Photoinduced Electron Transfer Oxygenations. In Topics in Current Chemistry: Photoinduced Electron Transfer I; Mattay, J., Ed.; Springer-Verlag: Berlin, 1990; Vol. 156, pp 117-166.
    • (1990) Topics in Current Chemistry: Photoinduced Electron Transfer I , vol.156 , pp. 117-166
    • Lopez, L.1
  • 44
    • 0344874462 scopus 로고    scopus 로고
    • note
    • 16b
  • 45
    • 0345305596 scopus 로고
    • Electron-transfer reactions in multicomponent systems
    • Gordon, M., Ware, W. R., Eds.; Academic: New York
    • (a) Farid, S.; Hartman, S. E.; Evans, T. R. Electron-Transfer Reactions in Multicomponent Systems. In The Exciplex; Gordon, M., Ware, W. R., Eds.; Academic: New York, 1975; pp 327-343.
    • (1975) The Exciplex , pp. 327-343
    • Farid, S.1    Hartman, S.E.2    Evans, T.R.3
  • 46
    • 0000227061 scopus 로고
    • Formation of an ozonide by electron-transfer photooxygenation of tetraphenyloxirane. Cosensitization by 9,10-dicyanoanthracene and biphenyl
    • (b) Schaap, A. P.; Lopez, L.; Gagnon, S. D. Formation of an Ozonide by Electron-Transfer Photooxygenation of Tetraphenyloxirane. Cosensitization by 9,10-Dicyanoanthracene and Biphenyl. J. Am. Chem. Soc. 1983, 105, 663-664.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 663-664
    • Schaap, A.P.1    Lopez, L.2    Gagnon, S.D.3
  • 47
    • 0012135151 scopus 로고
    • The electronic spectra of carbonium ions in strongly acidic solutions
    • Olah, G. A.; Pittman, C. U., Jr.; Waack, R.; Doran, M. The Electronic Spectra of Carbonium Ions in Strongly Acidic Solutions. J. Am. Chem. Soc. 1966, 88, 1488-1495.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 1488-1495
    • Olah, G.A.1    Pittman C.U., Jr.2    Waack, R.3    Doran, M.4
  • 48
    • 0039815723 scopus 로고
    • Transient phenomena in the photochemistry of trans-azocumene
    • Boate, D. R.; Scaiano, J. C. Transient Phenomena in the Photochemistry of trans-azocumene. Tetrahedron Lett. 1989, 30, 4633-4636.
    • (1989) Tetrahedron Lett. , vol.30 , pp. 4633-4636
    • Boate, D.R.1    Scaiano, J.C.2
  • 50
    • 0344874461 scopus 로고    scopus 로고
    • Master Thesis, Tohoku University
    • Hoshi, Y. Master Thesis, Tohoku University, 1998.
    • (1998)
    • Hoshi, Y.1
  • 52
    • 0020849942 scopus 로고
    • Photolysis of reluctant azoalkanes. Effect of structure on photochemical loss of nitrogen from 2,3-diazabicyclo[2.2.2]oct-2-ene derivatives
    • Engel, P. S.; Horsey, D. W.; Keys, D. E.; Nalepa, C. J.; Soltero, L. R. Photolysis of Reluctant Azoalkanes. Effect of Structure on Photochemical Loss of Nitrogen from 2,3-Diazabicyclo[2.2.2]oct-2-ene Derivatives. J. Am. Chem. Soc. 1983, 105, 7108-7114.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 7108-7114
    • Engel, P.S.1    Horsey, D.W.2    Keys, D.E.3    Nalepa, C.J.4    Soltero, L.R.5
  • 53
    • 33845551622 scopus 로고
    • Trimethylenemethane cation radical: Photosensitized (electron-transfer) generation and reactivity
    • (a) Takahashi, Y.; Miyashi, T.; Mukai, T. Trimethylenemethane Cation Radical: Photosensitized (Electron-Transfer) Generation and Reactivity. J. Am. Chem. Soc. 1983, 105, 6511-6513.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 6511-6513
    • Takahashi, Y.1    Miyashi, T.2    Mukai, T.3
  • 54
    • 0001504874 scopus 로고
    • Evidence for two different radical cation types derived from methylenecyclopropane
    • (b) Miyashi, T.; Takahashi, Y.; Mukai, T.; Roth, H. D.; Schilling, M. L. M. Evidence for Two Different Radical Cation Types Derived from Methylenecyclopropane. J. Am. Chem. Soc. 1985, 107, 1079-1080.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 1079-1080
    • Miyashi, T.1    Takahashi, Y.2    Mukai, T.3    Roth, H.D.4    Schilling, M.L.M.5
  • 55
    • 0000263310 scopus 로고
    • Electron-transfer photoreactions of small-ring compounds: Nature and role of cation-radical intermediates
    • (c) Miyashi, T.; Takahashi, Y.; Ohaku, H.; Ikeda, H.; Morishima, S.-I. Electron-Transfer Photoreactions of Small-Ring Compounds: Nature and Role of Cation-Radical Intermediates. Pure Appl. Chem. 1991, 63, 223-230.
    • (1991) Pure Appl. Chem. , vol.63 , pp. 223-230
    • Miyashi, T.1    Takahashi, Y.2    Ohaku, H.3    Ikeda, H.4    Morishima, S.-I.5
  • 56
    • 0032540650 scopus 로고    scopus 로고
    • Direct observation of two different types of TMM intermediates in the photoinduced electron-transfer degenerate methylenecyclopropane rearrangement
    • Ikeda, H.; Nakamura, T.; Miyashi, T.; Goodman, J. L.; Akiyama, K.; Tero-Kubota, S.; Houmam, A.; Wayner, D. D. M. Direct Observation of Two Different Types of TMM Intermediates in the Photoinduced Electron-Transfer Degenerate Methylenecyclopropane Rearrangement. J. Am. Chem. Soc. 1998, 120, 5832-5833.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 5832-5833
    • Ikeda, H.1    Nakamura, T.2    Miyashi, T.3    Goodman, J.L.4    Akiyama, K.5    Tero-Kubota, S.6    Houmam, A.7    Wayner, D.D.M.8
  • 57
    • 33845379032 scopus 로고
    • Simultaneous determination of photoreaction dynamics and energetics using pulsed, time-resolved photoacoustic calorimetry
    • Rudzki, J. E.; Goodman, J. L.; Peters, K. S. Simultaneous Determination of Photoreaction Dynamics and Energetics Using Pulsed, Time-Resolved Photoacoustic Calorimetry. J. Am. Chem. Soc. 1985, 107, 7849-7854. Herman, M. S.; Goodman, J. L. Determination of the Enthalpy and Reaction Volume Changes of Organic Photoreactions Using Photoacoustic Calorimetry. J. Am. Chem. Soc. 1989, 111, 1849-1854. Griller, D.; Wayner, D. D. M. Radical Thermochemistry and Organic Reactions. Pure Appl. Chem. 1989, 61, 717-724.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 7849-7854
    • Rudzki, J.E.1    Goodman, J.L.2    Peters, K.S.3
  • 58
    • 1542461045 scopus 로고
    • Determination of the enthalpy and reaction volume changes of organic photoreactions using photoacoustic calorimetry
    • Rudzki, J. E.; Goodman, J. L.; Peters, K. S. Simultaneous Determination of Photoreaction Dynamics and Energetics Using Pulsed, Time-Resolved Photoacoustic Calorimetry. J. Am. Chem. Soc. 1985, 107, 7849-7854. Herman, M. S.; Goodman, J. L. Determination of the Enthalpy and Reaction Volume Changes of Organic Photoreactions Using Photoacoustic Calorimetry. J. Am. Chem. Soc. 1989, 111, 1849-1854. Griller, D.; Wayner, D. D. M. Radical Thermochemistry and Organic Reactions. Pure Appl. Chem. 1989, 61, 717-724.
    • (1989) J. Am. Chem. Soc. , vol.111 , pp. 1849-1854
    • Herman, M.S.1    Goodman, J.L.2
  • 59
    • 0001214979 scopus 로고
    • Radical thermochemistry and organic reactions
    • Rudzki, J. E.; Goodman, J. L.; Peters, K. S. Simultaneous Determination of Photoreaction Dynamics and Energetics Using Pulsed, Time-Resolved Photoacoustic Calorimetry. J. Am. Chem. Soc. 1985, 107, 7849-7854. Herman, M. S.; Goodman, J. L. Determination of the Enthalpy and Reaction Volume Changes of Organic Photoreactions Using Photoacoustic Calorimetry. J. Am. Chem. Soc. 1989, 111, 1849-1854. Griller, D.; Wayner, D. D. M. Radical Thermochemistry and Organic Reactions. Pure Appl. Chem. 1989, 61, 717-724.
    • (1989) Pure Appl. Chem. , vol.61 , pp. 717-724
    • Griller, D.1    Wayner, D.D.M.2
  • 60
    • 0345305592 scopus 로고
    • Time-resolved photoacoustic calorimetry of carbenes and biradicals
    • Platz, M. S., Ed.; Plenum: New York; Chapter 2
    • For reviews of photoacoustic calorimetry, see, e.g.: Peters, K. S. Time-Resolved Photoacoustic Calorimetry of Carbenes and Biradicals. In Kinetics and Spectroscopy of Carbenes and Biradicals; Platz, M. S., Ed.; Plenum: New York, 1990; Chapter 2.
    • (1990) Kinetics and Spectroscopy of Carbenes and Biradicals
    • Peters, K.S.1
  • 61
    • 0033525488 scopus 로고    scopus 로고
    • Photoinduced electron-transfer cope rearrangements of 3,6-diaryl-2,6-octadienes and 2,5-diaryl-3,4-dimethyl-1,5-hexadienes: Stereospecificity and an unexpected formation of the bicyclo[2.2.0]hexane derivatives
    • Ikeda, H.; Takasaki, T.; Takahashi, Y.; Konno, A.; Matsumoto, M.; Hoshi, Y.; Aoki, T.; Suzuki, T.; Goodman, J. L.; Miyashi, T. Photoinduced Electron-Transfer Cope Rearrangements of 3,6-Diaryl-2,6-octadienes and 2,5-Diaryl-3,4-dimethyl-1,5-hexadienes: Stereospecificity and an Unexpected Formation of the Bicyclo[2.2.0]hexane Derivatives. J. Org. Chem. 1999, 64, 1640-1649.
    • (1999) J. Org. Chem. , vol.64 , pp. 1640-1649
    • Ikeda, H.1    Takasaki, T.2    Takahashi, Y.3    Konno, A.4    Matsumoto, M.5    Hoshi, Y.6    Aoki, T.7    Suzuki, T.8    Goodman, J.L.9    Miyashi, T.10
  • 62
    • 0041157024 scopus 로고    scopus 로고
    • The kinetically-controlled cope rearrangement of 2,5-bis(4-methoxyphenyl)-hexa-1,5-dienes induced by photosensitised electron transfer
    • Ikeda, H.; Ishida, A.; Takasaki, T.; Tojo, S.; Takamuku, S.; Miyashi, T. The Kinetically-Controlled Cope Rearrangement of 2,5-Bis(4-methoxyphenyl)-hexa-1,5-dienes Induced by Photosensitised Electron Transfer, J. Chem. Soc., Perkin Trans. 2 1997, 849-850.
    • (1997) J. Chem. Soc., Perkin Trans. 2 , pp. 849-850
    • Ikeda, H.1    Ishida, A.2    Takasaki, T.3    Tojo, S.4    Takamuku, S.5    Miyashi, T.6
  • 63
    • 0027531994 scopus 로고
    • Substitution effects on regioselective cyclizations of 1,5-and 2,4-diphenyl-1,5-hexadiene cation radicals generated by the electron-transfer photosensitizations
    • Ikeda, H.; Oikawa, T.; Miyashi, T. Substitution Effects on Regioselective Cyclizations of 1,5-and 2,4-Diphenyl-1,5-hexadiene Cation Radicals Generated by the Electron-Transfer Photosensitizations. Tetrahedron Lett. 1993, 34, 2323-2326.
    • (1993) Tetrahedron Lett. , vol.34 , pp. 2323-2326
    • Ikeda, H.1    Oikawa, T.2    Miyashi, T.3
  • 64
    • 0028247233 scopus 로고
    • Electron-transfer induced intramolecular [2 + 2] cycloaddition of 2,6-diarylhepta-1,6-dienes
    • Takahashi, Y.; Okitsu, O.; Ando, M.; Miyashi, T. Electron-Transfer Induced Intramolecular [2 + 2] Cycloaddition of 2,6-Diarylhepta-1,6-dienes. Tetrahedron Lett. 1994, 35, 3953-3956.
    • (1994) Tetrahedron Lett. , vol.35 , pp. 3953-3956
    • Takahashi, Y.1    Okitsu, O.2    Ando, M.3    Miyashi, T.4
  • 65
    • 0346294611 scopus 로고    scopus 로고
    • Photoinduced electron transfer (PET) cyclization and photooxygenation of 2,6-diaryl-1,6-heptadienes and 2,7-diaryl-1,7-octadienes
    • Griesbeck, A. G.; Sadlek, O.; Polborn, K. Photoinduced Electron Transfer (PET) Cyclization and Photooxygenation of 2,6-Diaryl-1,6-heptadienes and 2,7-Diaryl-1,7-octadienes. Liebigs Ann. 1996, 545-549.
    • (1996) Liebigs Ann. , pp. 545-549
    • Griesbeck, A.G.1    Sadlek, O.2    Polborn, K.3
  • 67
    • 37049084332 scopus 로고
    • Stepwise but potentially stereoselective intramolecular [2 + 2] cycloaddition of 2,6-diarylocata-1,6-dienes via a 1,4-cation radical intermediate
    • Takahashi, Y.; Ando, M.; Miyashi, T. Stepwise but Potentially Stereoselective Intramolecular [2 + 2] Cycloaddition of 2,6-Diarylocata-1,6-dienes via a 1,4-Cation Radical Intermediate. J. Chem. Soc., Chem. Commun. 1995, 521-522.
    • (1995) J. Chem. Soc., Chem. Commun. , pp. 521-522
    • Takahashi, Y.1    Ando, M.2    Miyashi, T.3
  • 68
    • 0028937361 scopus 로고
    • Photoinduced electron-transfer reactions of 2,7-diarylocta-1,7-dienes and 2,8-diarylnona-1,8-dienes
    • Takahashi, Y.; Ando, M.; Miyashi, T. Photoinduced Electron-Transfer Reactions of 2,7-Diarylocta-1,7-dienes and 2,8-Diarylnona-1,8-dienes. Tetrahedron Lett. 1995, 36, 1889-1892.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 1889-1892
    • Takahashi, Y.1    Ando, M.2    Miyashi, T.3
  • 69
    • 37049075001 scopus 로고
    • Generation of an o-xylylene: Electrocyclization of 1,2-bis(1-phenylvinyl)benzene promoted by photoinduced electron transfer
    • Takahashi, Y.; Ohya, Y.; Ikeda, H.; Miyashi, T. Generation of an o-Xylylene: Electrocyclization of 1,2-Bis(1-phenylvinyl)benzene Promoted by Photoinduced Electron Transfer. J. Chem. Soc., Chem. Commun. 1995, 1749-1750.
    • (1995) J. Chem. Soc., Chem. Commun. , pp. 1749-1750
    • Takahashi, Y.1    Ohya, Y.2    Ikeda, H.3    Miyashi, T.4
  • 70
    • 0344442589 scopus 로고
    • Master Thesis, Tohoku University
    • Yamada, M. Master Thesis, Tohoku University, 1993.
    • (1993)
    • Yamada, M.1
  • 71
    • 0344442588 scopus 로고
    • Master Thesis, Tohoku University
    • Ochiai, K. Master Thesis, Tohoku University, 1995.
    • (1995)
    • Ochiai, K.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.