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Volumn 72, Issue 5, 2007, Pages 1609-1616

Kinetic studies of a fast, reversible alkene radical cation cyclization reaction

Author keywords

[No Author keywords available]

Indexed keywords

ACYCLIC RADICAL CATIONS; KINETIC DETERMINATIONS; MESYLATE HETEROLYSIS;

EID: 33847691500     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo061868w     Document Type: Article
Times cited : (7)

References (46)
  • 8
    • 0001271574 scopus 로고    scopus 로고
    • Renaud, P, Sibi, M. P, Eds, Wiley-VCH: Weinheim
    • Crich, D. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, 2001; Vol. 2, pp 188-206.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 188-206
    • Crich, D.1
  • 12
    • 9444221344 scopus 로고    scopus 로고
    • See:, and references therein
    • See: Huang, Y. T.; Moeller, K. D. Org. Lett. 2004, 6, 4199-4202 and references therein.
    • (2004) Org. Lett , vol.6 , pp. 4199-4202
    • Huang, Y.T.1    Moeller, K.D.2
  • 18
    • 33847611698 scopus 로고    scopus 로고
    • PTOC is an abbreviation for pyridine-2-thioneoxycarbonyl. PTOC esters react in chain reactions to give acyloxyl radicals that rapidly decarboxylate to give alkyl radicals. For details, see ref 19
    • PTOC is an abbreviation for pyridine-2-thioneoxycarbonyl. PTOC esters react in chain reactions to give acyloxyl radicals that rapidly decarboxylate to give alkyl radicals. For details, see ref 19.
  • 21
    • 33847676949 scopus 로고    scopus 로고
    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Zakrzewski, V. G, Montgomery, J. A, Jr, Stratmann, R. E, Burant, J. C, Dapprich, S, Millam, J. M, Daniels, A. D, Kudin, K. N, Strain, M. C, Farkas, O, Tomasi, J, Barone, V, Cossi, M, Cammi, R, Mennucci, B, Pomelli, C, Adamo, C, Clifford, S, Ochterski, J, Petersson, G. A, Ayala, P. Y, Cui, Q, Morokuma, K, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Cioslowski, J, Ortiz, J. V, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Gomperts, R, Martin, R. L, Fox, D. J, Keith, T, Al-Laham, M. A, Peng, C. Y, Nanayakkara, A, Gonzalez, C, Challacombe, M, Gill, P. M. W, Johnson, B. G, Chen, W, Wong, M. W, Andres, J. L, Head-Gordon, M, Replogle, E. S, Pople, J. A. Gaussian 98, revision A.9; Gaussian, Inc, Pittsburgh, PA, 1998
    • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Zakrzewski, V. G.; Montgomery, J. A., Jr.; Stratmann, R. E.; Burant, J. C.; Dapprich, S.; Millam, J. M.; Daniels, A. D.; Kudin, K. N.; Strain, M. C.; Farkas, O.; Tomasi, J.; Barone, V.; Cossi, M.; Cammi, R.; Mennucci, B.; Pomelli, C.; Adamo, C.; Clifford, S.; Ochterski, J.; Petersson, G. A.; Ayala, P. Y.; Cui, Q.; Morokuma, K.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Cioslowski, J.; Ortiz, J. V.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Gomperts, R.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Gonzalez, C.; Challacombe, M.; Gill, P. M. W.; Johnson, B. G.; Chen, W.; Wong, M. W.; Andres, J. L.; Head-Gordon, M.; Replogle, E. S.; Pople, J. A. Gaussian 98, revision A.9; Gaussian, Inc.: Pittsburgh, PA, 1998.
  • 22
    • 33847612142 scopus 로고    scopus 로고
    • We judge the results to be reliable at the semiquantitative level because similar computations for isodesmic reactions of alkenes with known ionization potentials with an ethylene radical cation had average errors of 2.2 kcal/mol; see Supporting Information
    • We judge the results to be reliable at the semiquantitative level because similar computations for isodesmic reactions of alkenes with known ionization potentials with an ethylene radical cation had average errors of 2.2 kcal/mol; see Supporting Information.
  • 39
  • 42
    • 33847620892 scopus 로고    scopus 로고
    • An expectation that 1,1-diaryl alkene radical cations will absorb strongly at ca. 400 nm might be based on limited data. For example, PET oxidation of 1,1-diphenylethene and 1,1-diphenylbut-1-ene by the chloranil triplet in CH3CN solution gave results similar to those with diene 10. Weak signals centered at ca. 400 nm were observed
    • 3CN solution gave results similar to those with diene 10. Weak signals centered at ca. 400 nm were observed.
  • 44
    • 33847607178 scopus 로고    scopus 로고
    • PSI-Plot, version 7.01 for Windows; Poly Software International Inc, Pearl River, NY, 2002
    • PSI-Plot, version 7.01 for Windows; Poly Software International Inc.: Pearl River, NY, 2002.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.