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Volumn 73, Issue 4, 2008, Pages 1413-1421

N-centered radicals in self-terminating radical cyclizations: Experimental and computational studies

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; KETONES; PHOTOCHEMICAL REACTIONS;

EID: 39349104550     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702261u     Document Type: Article
Times cited : (31)

References (55)
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    • Reviews on N-centered radicals: (a) Wolf, M. E
    • Reviews on N-centered radicals: (a) Wolf, M. E. Chem. Rev. 1963, 63, 55.
    • (1963) Chem. Rev , vol.63 , pp. 55
  • 26
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    • It was verified that 1 was completely consumed after 60 min of irradiation time.
    • It was verified that 1 was completely consumed after 60 min of irradiation time.
  • 27
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    • The ketones 7a and 8a were unambiguously identified by comparison of their GC retention times with those of authentic samples, in addition to GC/MS experiments.
    • The ketones 7a and 8a were unambiguously identified by comparison of their GC retention times with those of authentic samples, in addition to GC/MS experiments.
  • 28
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    • Attempts to trap N-containing intermediates, for example through in situ reduction of imines with sodium borohydride, were not successful.
    • Attempts to trap N-containing intermediates, for example through in situ reduction of imines with sodium borohydride, were not successful.
  • 30
    • 39349103007 scopus 로고    scopus 로고
    • GC analysis of the crude, acidic reaction mixture was not possible
    • GC analysis of the crude, acidic reaction mixture was not possible.
  • 31
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    • -1; see for example: (a) Turro, N. J.; Gould, I. R.; Baretz, B. H. J. Phys. Chem. 1983, 87, 531.
    • -1; see for example: (a) Turro, N. J.; Gould, I. R.; Baretz, B. H. J. Phys. Chem. 1983, 87, 531.
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    • Ph.D. Thesis, Universität Kiel
    • Dreessen, T. Ph.D. Thesis, Universität Kiel, 2004.
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    • Dreessen, T.1
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    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery, J. A, Jr, Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, Iyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Martin, R. L, Fox, D. J, Keith, T, Al-Laham
    • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision B.04; Gaussian, Inc.: Pittsburgh, PA, 2003.
  • 35
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    • Single-point energy calculations performed with the QCISD/cc-pVDZ and CCSDT/cc-pVDZ methods on BHandHLYP/6-311G** and BHandHLYP/aug-cc- pVTZ optimized geometries showed excellent agreement with results obtained from BHandHLYP/6-311G** and BHandHLYP/6-311++G** computations
    • Single-point energy calculations performed with the QCISD/cc-pVDZ and CCSDT/cc-pVDZ methods on BHandHLYP/6-311G** and BHandHLYP/aug-cc- pVTZ optimized geometries showed excellent agreement with results obtained from BHandHLYP/6-311G** and BHandHLYP/6-311++G** computations.
  • 37
    • 39349093093 scopus 로고    scopus 로고
    • Orienting computations have revealed that the energetics of the parallel pathway leading to the bicyclo[5.3.0]decane derivative 7b via a 1,5-HAT and 5-exo cyclization are in the same order of magnitude
    • Orienting computations have revealed that the energetics of the parallel pathway leading to the bicyclo[5.3.0]decane derivative 7b via a 1,5-HAT and 5-exo cyclization are in the same order of magnitude.
  • 38
    • 39349109383 scopus 로고    scopus 로고
    • -1 lower in energy than the free reactants.
    • -1 lower in energy than the free reactants.
  • 39
    • 39349110319 scopus 로고    scopus 로고
    • 2 during the radical addition.
    • 2 during the radical addition.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.