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Volumn 60, Issue 6, 2007, Pages 420-428

Oxidation of aromatic alkynes with nitrate radicals (NO3 •): An experimental and computational study on a synthetically highly versatile radical

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; KETONES; NITRATES; OXIDATION; PHOTOCHEMICAL REACTIONS; AROMATIC COMPOUNDS; DENSITY FUNCTIONAL THEORY;

EID: 34250835865     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH07045     Document Type: Article
Times cited : (20)

References (42)
  • 1
    • 0033551813 scopus 로고    scopus 로고
    • doi:10.1016/ S0040-4020(99)00564-5
    • (a) U. Wille, L. Lietzau, Tetrahedron 1999, 55, 10119. doi:10.1016/ S0040-4020(99)00564-5
    • (1999) Tetrahedron , vol.55 , pp. 10119
    • Wille, U.1    Lietzau, L.2
  • 4
    • 0037126994 scopus 로고    scopus 로고
    • U. Wille, Chem. Eur. J. 2002, 8, 340. doi:10.1002/1521-3765(20020118)8:2〈340::AID-CHEM340〉3.0.CO;2-4
    • (a) U. Wille, Chem. Eur. J. 2002, 8, 340. doi:10.1002/1521-3765(20020118)8:2〈340::AID-CHEM340〉3.0.CO;2-4
  • 6
    • 34250833600 scopus 로고    scopus 로고
    • Ph.D. Thesis, University of Kiel: Kiel
    • L. Lietzau, Ph.D. Thesis 1999 (University of Kiel: Kiel).
    • (1999)
    • Lietzau, L.1
  • 7
  • 9
    • 33751156747 scopus 로고
    • doi:10.1021/JO00129A010
    • (c) Z. L. Zhu, J. H. Espenson, J. Org. Chem. 1995, 60, 7728. doi:10.1021/JO00129A010
    • (1995) J. Org. Chem , vol.60 , pp. 7728
    • Zhu, Z.L.1    Espenson, J.H.2
  • 12
    • 34250845540 scopus 로고    scopus 로고
    • Mass Spectra in NIST Chemistry WebBook, NIST Standard Reference Database Number 69 (Eds P. J. Linstrom, W. G. Mallard) 2005 (National Institute of Standards and Technology: Gaithersburg, MD). http://webbook.nist.gov
    • Mass Spectra in NIST Chemistry WebBook, NIST Standard Reference Database Number 69 (Eds P. J. Linstrom, W. G. Mallard) 2005 (National Institute of Standards and Technology: Gaithersburg, MD). http://webbook.nist.gov
  • 14
  • 15
    • 34250897027 scopus 로고    scopus 로고
    • We have also studied the reaction of NO3. with mixed aryl-alkyl, dialkyl, and terminal aromatic alkynes. However, numerous products were obtained in each case, which were not further investigated
    • . with mixed aryl-alkyl, dialkyl, and terminal aromatic alkynes. However, numerous products were obtained in each case, which were not further investigated.
  • 16
    • 34250806227 scopus 로고    scopus 로고
    • ..
    • ..
  • 18
    • 0003260139 scopus 로고    scopus 로고
    • doi:10.1021/OL006527Y
    • U. Wille, Org. Lett. 2000, 2, 3485. doi:10.1021/OL006527Y
    • (2000) Org. Lett , vol.2 , pp. 3485
    • Wille, U.1
  • 19
    • 33845551924 scopus 로고
    • doi:10.1021/ CR00057A002
    • (a) E. G. Lewars, Chem. Rev. 1983, 83, 519. doi:10.1021/ CR00057A002
    • (1983) Chem. Rev , vol.83 , pp. 519
    • Lewars, E.G.1
  • 22
    • 34250881250 scopus 로고    scopus 로고
    • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr, T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, T. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Kiene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M
    • M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, J. A. Montgomery, Jr., T. Vreven, K. N. Kudin, J. C. Burant, J. M. Millam, S. S. Iyengar, .T. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G. A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Kiene, X. Li, J. E. Knox, H. P. Hratchian, J. B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R. E. Stratmann, O. Yazyev, A. J. Austin, R. Cammi, C. Pomelli, J. W. Ochterski, P. Y. Ayala, K. Morokuma, G. A. Voth, P. Salvador, J. J. Dannenberg, V. G. Zakrzewski, S. Dapprich, A. D. Daniels, M. C. Strain, O. Farkas, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. V. Ortiz, Q. Cui, A. G. Baboul, S. Clifford, J. Cioslowski, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, C. Gonzalez, J. A. Pople, Gaussian 03, Revision D.01 2004, (Gaussian, Inc.: Wallingford, CT).
  • 23
    • 34250885397 scopus 로고
    • doi:10.1016/ S0040-4020(01)83028-3
    • (a)T.W.Koenig, T.Barklow, Tetrahedron 1969, 25, 4875. doi:10.1016/ S0040-4020(01)83028-3
    • (1969) Tetrahedron , vol.25 , pp. 4875
    • Koenig, T.W.1    Barklow, T.2
  • 25
    • 33646937115 scopus 로고    scopus 로고
    • doi:10.1021/JO0520543
    • U. Wille, J. Org. Chem. 2006, 71, 4040. doi:10.1021/JO0520543
    • (2006) J. Org. Chem , vol.71 , pp. 4040
    • Wille, U.1
  • 26
    • 34250822549 scopus 로고    scopus 로고
    • The geometries computed at the various levels of theory were found to vary only insignificantly
    • The geometries computed at the various levels of theory were found to vary only insignificantly.
  • 27
    • 34250903832 scopus 로고    scopus 로고
    • -1 than the Z isomer:
    • -1 than the Z isomer:
  • 28
  • 29
    • 34250888387 scopus 로고    scopus 로고
    • J. Fossey, D. Lefort, J. Sorba, Free Radicals in Organic Chemistry 1995 (John Wiley & Sons: Chichester). For convenience, we have used in this work the E-configured vinyl radical 121 as energetic reference, because no configurational change at the C=C double bond is required in going from 121 to 141 via transition state 131.
    • (b) J. Fossey, D. Lefort, J. Sorba, Free Radicals in Organic Chemistry 1995 (John Wiley & Sons: Chichester). For convenience, we have used in this work the E-configured vinyl radical 121 as energetic reference, because no configurational change at the C=C double bond is required in going from 121 to 141 via transition state 131.
  • 30
    • 34250793582 scopus 로고    scopus 로고
    • Solvation effects, which were calculated using the PCM model as implemented in Gaussian03 did not result in significant changes of the barrier heights of any transition state 13 and 16, respectively.
    • Solvation effects, which were calculated using the PCM model as implemented in Gaussian03 did not result in significant changes of the barrier heights of any transition state 13 and 16, respectively.
  • 31
    • 5244245983 scopus 로고
    • doi:10.1021/ JA01607A027
    • G. S. Hammond, J. Am. Chem. Soc. 1955, 77, 334. doi:10.1021/ JA01607A027
    • (1955) J. Am. Chem. Soc , vol.77 , pp. 334
    • Hammond, G.S.1
  • 32
    • 0028761729 scopus 로고    scopus 로고
    • This rearrangement has been calculated using methods involving high levels of electron correlation and basis sets; see for example: (a) A. P. Scott, R. H. Nobes, H. F. Schaefer, III, L. Radom, J. Am. Chem. Soc. 1994, 116, 10159. doi:10.1021/JA00101A039
    • This rearrangement has been calculated using methods involving high levels of electron correlation and basis sets; see for example: (a) A. P. Scott, R. H. Nobes, H. F. Schaefer, III, L. Radom, J. Am. Chem. Soc. 1994, 116, 10159. doi:10.1021/JA00101A039
  • 33
    • 0037028613 scopus 로고    scopus 로고
    • doi:10.1016/S0009-2614(01)01496-8
    • (b) P. J. Wilson, D. J. Tozer, Chem. Phys. Lett. 2002, 352, 540. doi:10.1016/S0009-2614(01)01496-8
    • (2002) Chem. Phys. Lett , vol.352 , pp. 540
    • Wilson, P.J.1    Tozer, D.J.2
  • 35
    • 34250823157 scopus 로고    scopus 로고
    • We did not investigate whether the reaction of NO3. with alkynes in the presence of excess NO3. leads to exclusive formation of 1,2-diketones, in order to support the assumed reversibility of the γ-fragmentation 12→17. Under such conditions, NO3. is trapped by NO2. to give N2O5, thus rendering this experiment insignificant
    • 5, thus rendering this experiment insignificant.
  • 37
    • 34250817729 scopus 로고    scopus 로고
    • . are therefore highly unlikely.
    • . are therefore highly unlikely.
  • 39
    • 0004251017 scopus 로고
    • Eds N. Brenner, J. E. Callen, M. D. Weiss, Academic Press: New York, NY
    • (a) J. C. Sternberg, W. S. Gallaway, D. T. L. Jones, Gas Chromatography (Eds N. Brenner, J. E. Callen, M. D. Weiss) 1962 (Academic Press: New York, NY).
    • (1962) Gas Chromatography
    • Sternberg, J.C.1    Gallaway, W.S.2    Jones, D.T.L.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.