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Volumn 118, Issue 1, 1996, Pages 140-154

Photoinduced electron transfer reactions of aryl olefins. 2. Cis-trans isomerization and cycloadduct formation in anethole-fumaronitrile systems in polar solvents

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EID: 0000999950     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9511578     Document Type: Article
Times cited : (30)

References (103)
  • 6
    • 0002559356 scopus 로고
    • Padwa, A., Ed.; Marcel Dekker: New York
    • See, for instance: (a) Jones, G. In Organic Photochemistry, Padwa, A., Ed.; Marcel Dekker: New York, 1981; Vol. 5, pp 1-122.
    • (1981) Organic Photochemistry , vol.5 , pp. 1-122
    • Jones, G.1
  • 7
    • 84987528041 scopus 로고
    • and references therein
    • (b) Demuth, M.; Mikhail, G. Synthesis 1989, 145-162, and references therein.
    • (1989) Synthesis , pp. 145-162
    • Demuth, M.1    Mikhail, G.2
  • 27
    • 5344276680 scopus 로고    scopus 로고
    • (a) Roth, H. D. in ref 14d, pp 53-61
    • (a) Roth, H. D. in ref 14d, pp 53-61.
  • 30
    • 5344225718 scopus 로고
    • Closs, G. L.; Miller, R. J. J Am. Chem. Soc. 1979, 101, 1639-1641; 1981, 103, 3586-3588.
    • (1981) J Am. Chem. Soc. , vol.103 , pp. 3586-3588
  • 45
    • 5344251088 scopus 로고    scopus 로고
    • note
    • We should like to emphasize that the product distribution observed in these experiments does not unambiguously rule out that tA and cA react to different products: With our reactants cycloaddition is accompanied by geometric isomerization of the substrate to a large degree. so under conditions of preparative photolysis the system moves far towards the photostationary equilibrium between tA and cA regardless of whether the starting anethole is cA or tA. However, the same product distribution is also found in the CIDNP experiments described below, which are performed at very low conversion of the substrate.
  • 49
    • 5344234876 scopus 로고    scopus 로고
    • For photoinduced electron transfer sensitization in a similar reaction system see ref 13
    • For photoinduced electron transfer sensitization in a similar reaction system see ref 13.
  • 52
    • 5344279208 scopus 로고
    • Ph.D. Thesis, Braunschweig
    • 3CNA.
    • (1995)
    • Ecken, G.1
  • 56
    • 33847085070 scopus 로고
    • According to the usual definition of ε. this parameter is taken to denote the mode of product formation (ε = +1, cage reaction; ε = -1, reaction of escaping radicals). This interpretation is appealing to chemists because it is directly linked to mechanistic concepts; very often it is also permissible, since for the majority of radical pairs cage recombination can take place in the singlet state only. In reactions involving radical ion pairs, however, geminate processes of pairs of either multiplicity are frequently possible, so the assignment of ε (Roth, H. D.; Manion-Schilling, M. L. J. Am. Chem. Soc. 1980, 102, 4303-4310) adopted here must be used.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 4303-4310
    • Roth, H.D.1    Manion-Schilling, M.L.2
  • 62
    • 85088229596 scopus 로고
    • Ph.D. Thesis, Braunschweig
    • •- on a time scale of 10 μs (Eckert. G. Ph.D. Thesis, Braunschweig, 1995).
    • (1995)
    • Eckert, G.1
  • 63
    • 5344244840 scopus 로고    scopus 로고
    • note
    • 15a
  • 64
    • 85088226419 scopus 로고    scopus 로고
    • note
    • 65
  • 65
    • 5344243255 scopus 로고    scopus 로고
    • note
    • 3tA or tA from the cation or the anion. This argument can be extended to isomerization via bond rotation in a triplet biradical followed by biradical cleavage
  • 74
    • 5344241307 scopus 로고    scopus 로고
    • Bargon, J. in ref 14d. pp 393-398
    • Bargon, J. in ref 14d. pp 393-398.
  • 93
    • 5344221683 scopus 로고    scopus 로고
    • note
    • -1.
  • 94
    • 5344271919 scopus 로고    scopus 로고
    • note
    • 3BR and all their subsequent products. In evaluations of relative polarizations stemming from the anethole radical cation only, this reaction is thus unimportant. The same argument can be used to explain why omission of escaping radical ions does not influence relative polarizations as long as no relaxation losses occur.
  • 95
    • 5344244140 scopus 로고    scopus 로고
    • Manuscript in preparation
    • Eckert, G.; Goez, M. Manuscript in preparation.
    • Eckert, G.1    Goez, M.2
  • 101
    • 0011688837 scopus 로고
    • Goez, M. Chem. Phys, 1990, 147, 143-154.
    • (1990) Chem. Phys , vol.147 , pp. 143-154
    • Goez, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.