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Volumn 73, Issue 22, 2008, Pages 8815-8828

Photochemical C2-C6 cyclization of enyne-allenes: Detection of a fulvene triplet diradical in the laser flash photolysis

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTIONS; DENSITY FUNCTIONAL THEORY; OXYGEN; PHOTOLYSIS; PROBABILITY DENSITY FUNCTION; QUENCHING;

EID: 56549110014     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo801689w     Document Type: Article
Times cited : (33)

References (71)
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    • Mody, T. M, Sessler, J. L, Eds, Wiley: Chichester, U.K
    • (b) Mody, T. M., Sessler, J. L., Eds. Supramolecular Materials and Technologies; Wiley: Chichester, U.K., 1999; Vol. 4.
    • (1999) Supramolecular Materials and Technologies , vol.4
  • 22
    • 56549129078 scopus 로고    scopus 로고
    • Private communication by Prof. B. Engels
    • Private communication by Prof. B. Engels.
  • 30
    • 56549125959 scopus 로고    scopus 로고
    • For the synthesis of compound 2 see: (a) Arnold, Z.; Holy, A. Collect. Czech. Chem. Commun. 1961, 26, 3059-3073.
    • For the synthesis of compound 2 see: (a) Arnold, Z.; Holy, A. Collect. Czech. Chem. Commun. 1961, 26, 3059-3073.
  • 35
    • 33845552159 scopus 로고    scopus 로고
    • Elsevier, C. J.; Stehouwer, P. M.; Westmijze, H.; Vermeer, P. J. Org. Chem. 1983, 48, 1103-1105. For the synthesis of 1a, see: ref 13.
    • Elsevier, C. J.; Stehouwer, P. M.; Westmijze, H.; Vermeer, P. J. Org. Chem. 1983, 48, 1103-1105. For the synthesis of 1a, see: ref 13.
  • 44
    • 56549090539 scopus 로고    scopus 로고
    • 6 product 8b′. This was tested by independent irradiation of 8b′ (isolated from the thermal reaction).
    • 6 product 8b′. This was tested by independent irradiation of 8b′ (isolated from the thermal reaction).
  • 46
    • 56549122673 scopus 로고    scopus 로고
    • 6 product (9d-1) could not be clarified.
    • 6 product (9d-1) could not be clarified.
  • 47
    • 32244432511 scopus 로고
    • 2nd ed, Murov, S. L, Carmichael, I, Hug, G. L, Eds, Marcel Dekker/CRC Press: Boca Raton
    • Handbook of photochemistry, 2nd ed.; Murov, S. L., Carmichael, I., Hug, G. L., Eds.; Marcel Dekker/CRC Press: Boca Raton, 1993.
    • (1993) Handbook of photochemistry
  • 49
    • 56549091538 scopus 로고    scopus 로고
    • Errors in calculated spectra are larger at long wavelengths (an energy difference corresponding to 20 nm wavelength difference at λ = 200 nm amounts to 100 nm wavelength difference at λ = 1000 nm). Our omission of the remote bromine atom substituents may also contribute to deviations between calculated and experimental spectra.
    • (a) Errors in calculated spectra are larger at long wavelengths (an energy difference corresponding to 20 nm wavelength difference at λ = 200 nm amounts to 100 nm wavelength difference at λ = 1000 nm). Our omission of the remote bromine atom substituents may also contribute to deviations between calculated and experimental spectra.
  • 50
    • 56549126217 scopus 로고    scopus 로고
    • This statement also holds, if the biradicals and final products are included into the consideration. For the SP energies, see the Supporting Information
    • (b) This statement also holds, if the biradicals and final products are included into the consideration. For the SP energies, see the Supporting Information.
  • 55
    • 56549123218 scopus 로고    scopus 로고
    • Oxygen attack at other positions is less favorable
    • Oxygen attack at other positions is less favorable.
  • 59
    • 56549129077 scopus 로고    scopus 로고
    • Compared to the experimental system, only the n-butyl group has been replaced by a methyl group in 15. An alternative dihydrocarbazole triplet 15b, where the ring closure reaction involves the benzene ring connected to the allene moiety, is calculated to be higher in energy than 15.
    • (d) Compared to the experimental system, only the n-butyl group has been replaced by a methyl group in 15. An alternative dihydrocarbazole triplet 15b, where the ring closure reaction involves the benzene ring connected to the allene moiety, is calculated to be higher in energy than 15.
  • 63
    • 21144470378 scopus 로고    scopus 로고
    • Gaussian, Inc, Wallingford, CT
    • Frisch, M. J. et al. Gaussian03; Gaussian, Inc.: Wallingford, CT, 2004.
    • (2004) Gaussian03
    • Frisch, M.J.1
  • 71
    • 56549093028 scopus 로고    scopus 로고
    • University of Karlsruhe: Karlsruhe
    • TURBOMOLE V5-9-1; University of Karlsruhe: Karlsruhe, 2007.
    • (2007) TURBOMOLE V5-9-1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.