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Volumn , Issue 21, 2003, Pages 4248-4264

Proximate, "Parallel-In-Plane" Preoriented Bis(diazenes) - In-Plane Delocalized Bis(homoconjugated) 4N/5(6)e Anions

Author keywords

Azo compounds; Cyclic voltammetry; Density functional calculations; Homoconjugation

Indexed keywords

ANION; AZO COMPOUND;

EID: 0242427557     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200300298     Document Type: Article
Times cited : (10)

References (101)
  • 5
    • 0242605779 scopus 로고    scopus 로고
    • Dissertations (University of Freiburg): [a] G. Fischer, 1987 (Diplomarbeit, 1982)
    • Dissertations (University of Freiburg): [a] G. Fischer, 1987 (Diplomarbeit, 1982).
  • 6
    • 0242437457 scopus 로고    scopus 로고
    • [b] E. Beckmann, 1991
    • [b] E. Beckmann, 1991.
  • 7
    • 0242521019 scopus 로고    scopus 로고
    • [c] N. Bahr, 1994
    • [c] N. Bahr, 1994.
  • 8
    • 0242437456 scopus 로고    scopus 로고
    • [d] M. Lugan, 1994
    • [d] M. Lugan, 1994.
  • 9
    • 0242605778 scopus 로고    scopus 로고
    • [e] O. Cullmann, 1997 (Diplomarbeit 1994)
    • [e] O. Cullmann, 1997 (Diplomarbeit 1994).
  • 10
    • 0242605777 scopus 로고    scopus 로고
    • [f] M. Exner, 1994
    • [f] M. Exner, 1994.
  • 11
    • 0242437458 scopus 로고    scopus 로고
    • [g] M. Vögtle, 2000
    • [g] M. Vögtle, 2000.
  • 12
    • 0242689795 scopus 로고    scopus 로고
    • [h] M. Kegel, 2001
    • [h] M. Kegel, 2001.
  • 13
    • 0242521034 scopus 로고    scopus 로고
    • [i] Research reports of Dr. F. Yang (Humboldt Fellow 1993-1999)
    • [i] Research reports of Dr. F. Yang (Humboldt Fellow 1993-1999).
  • 16
    • 0242437459 scopus 로고    scopus 로고
    • See ref. [2,3] in ref.[13]
    • See ref. [2,3] in ref.[13]
  • 17
    • 0242605775 scopus 로고
    • (Allinger-QCPE 395). + MMP1 (Allinger - QCPE 318)+ more atoms and constants by K. E. Gilbert and J. J. Gajewski, Indiana University
    • MMX version 87.200: MM2 1977(Allinger-QCPE 395). + MMP1 (Allinger - QCPE 318)+ more atoms and constants by K. E. Gilbert and J. J. Gajewski, Indiana University, 1987.
    • (1977) MMX Version 87.200: MM2
  • 19
    • 0242437467 scopus 로고
    • University of Freiburg
    • [b] K. Exner, Diplomarbeit, University of Freiburg, 1995.
    • (1995) Diplomarbeit
    • Exner, K.1
  • 21
    • 0000189651 scopus 로고
    • Gaussian 94, Revision E.2, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1995. B3LYP cf,: A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652; C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648-5652
    • Becke, A.D.1
  • 22
    • 0345491105 scopus 로고
    • Gaussian 94, Revision E.2, M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, and J. A. Pople, Gaussian, Inc., Pittsburgh PA, 1995. B3LYP cf,: A. D. Becke, J. Chem. Phys. 1993, 98, 5648-5652; C. Lee, W. Yang, R. G. Parr, Phys. Rev. B 1988, 37, 785-789.
    • (1988) Phys. Rev. B , vol.37 , pp. 785-789
    • Lee, C.1    Yang, W.2    Parr, R.G.3
  • 23
    • 0242605787 scopus 로고    scopus 로고
    • See ref.[7-11] in ref.[9]
    • See ref.[7-11] in ref.[9]
  • 26
    • 0242521031 scopus 로고    scopus 로고
    • note
    • Reversible formation of [2 + 2] cycloadducts for the C-/D-bis(diazenes) [and all bis(diazene) N-Oxides] cannot be rigorously ruled out. In fact, the very slow conversion of one or the other substrate is suggestive of unproductive consumption of light.
  • 29
    • 0030444987 scopus 로고    scopus 로고
    • [b] K. Exner, D. Hochstrate, M. Keller, F.-G. Klärner, H. Prinzbach, Angew. Chem. 1996, 108, 2399-2402; Angew. Chem. Int. Ed. Engl. 1996, 35, 2256-2259.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.35 , pp. 2256-2259
  • 36
    • 0242521032 scopus 로고    scopus 로고
    • K. Exner, D. Hunkler, G. Gescheidt, H. Prinzbach, Angew. Chem. 1998, 110, 2012-2016; Angew. Chem. Int. Ed. Engl. 1996, 37, 1910-1913.
    • (1996) Angew. Chem. Int. Ed. Engl. , vol.37 , pp. 1910-1913
  • 39
    • 0034619118 scopus 로고    scopus 로고
    • 2-symmetrical bisanion); [2g] α-peralkylated analogues could not be constructed. For azine bridges as conjugation stoppers see: P. Zuman, J. Ludvik, Tetrahedron Lett. 2000, 41, 7851-7853. M. Lewis, R. Glaser, J. Org Chem. 2002,. 67, 1441-1447. EQUATION PRESENTATION
    • (2000) Tetrahedron Lett. , vol.41 , pp. 7851-7853
    • Zuman, P.1    Ludvik, J.2
  • 40
    • 0037040646 scopus 로고    scopus 로고
    • EQUATION PRESENTATION
    • 2-symmetrical bisanion); [2g] α-peralkylated analogues could not be constructed. For azine bridges as conjugation stoppers see: P. Zuman, J. Ludvik, Tetrahedron Lett. 2000, 41, 7851-7853. M. Lewis, R. Glaser, J. Org Chem. 2002,. 67, 1441-1447. EQUATION PRESENTATION
    • (2002) J. Org Chem. , vol.67 , pp. 1441-1447
    • Lewis, M.1    Glaser, R.2
  • 46
    • 0040784287 scopus 로고    scopus 로고
    • [c] K. Exner, B. Groβmann, G. Gescheidt, J. Heinze, M. Keller, T. Bally, P. Bednarek, H. Prinzbach, Angew. Chem. 2000, 112, 1514-1517; Angew. Chem. Int. Ed. 2000, 39, 1455-1458.
    • (2000) Angew. Chem. Int. Ed. , vol.39 , pp. 1455-1458
  • 47
    • 0242689809 scopus 로고    scopus 로고
    • note
    • 2, d = 4.75 Å} σ complexes had resulted.[23a]
  • 49
    • 0242689797 scopus 로고    scopus 로고
    • note
    • Once various B-type bis(diazene) N-oxides had become available as photoproducts of their A-type isomers,[13] their deoxygenation seemed a convenient route to the respective bis(diazenes). In line with literature reports, [14] however, strain-related complications made this approach impractical.
  • 55
    • 0242605784 scopus 로고    scopus 로고
    • note
    • The intricacies of the multistep hydrazine reaction were once more evident when under the conditions of the neat transformation 1b → 3b the respective 2,8-dione[24] delivered only polymers.
  • 58
    • 33644517707 scopus 로고
    • (Ed.: B. M. Trost), Pergamon Press, Oxford
    • [b] S. V. Ley, A. Madin, Comprehensive Organic Synthesis, (Ed.: B. M. Trost), Vol. 7, Pergamon Press, Oxford, 1991, 252-289.
    • (1991) Comprehensive Organic Synthesis , vol.7 , pp. 252-289
    • Ley, S.V.1    Madin, A.2
  • 59
    • 0000421996 scopus 로고
    • (Ed.: B. M. Trost), Pergamon Press, Oxford
    • Rev.: T. Immamoto, Comprehensive Organic Synthesis, (Ed.: B. M. Trost), Vol. 1, Pergamon Press, Oxford, 1991, 231-250.
    • (1991) Comprehensive Organic Synthesis , vol.1 , pp. 231-250
    • Immamoto, T.1
  • 68
    • 84989521539 scopus 로고
    • [a] R. Link, R. Schwesinger, Angew. Chem. 1992, 31, 864; Angew. Chem. Int. Ed. Engl. 1992, 31, 850.
    • (1992) Angew. Chem. Int. Ed. Engl. , vol.31 , pp. 850
  • 70
    • 33748869136 scopus 로고
    • [b] R. Schwesinger, R. Link, G. Thiele, H. Rotter, D. Honert, H.-H. Limbach, F. Männle, Angew. Chem. 1991, 101, 1376-1378; Angew. Chem. Int. Ed. Engl. 1991, 30, 1372-1374.
    • (1991) Angew. Chem. Int. Ed. Engl. , vol.30 , pp. 1372-1374
  • 71
    • 0001405464 scopus 로고
    • (Eds.: E. L. Eliel, S. H. Wilen), John Wiley & sons, New York
    • [a] Rev.: W. Luef, R. Keese, in Topics in Stereochemistry, Vol. 20, (Eds.: E. L. Eliel, S. H. Wilen), John Wiley & sons, New York, 1991, 231.
    • (1991) Topics in Stereochemistry , vol.20 , pp. 231
    • Luef, W.1    Keese, R.2
  • 79
    • 0242689805 scopus 로고    scopus 로고
    • note
    • CCDC ref. codes KEMGUE (20),[36] 188159 (34a), 188160 (34d), and 188162 (33d) contain the supplementary crystallographic data for this paper. These data can be obtained free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html [or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB2 1EZ, UK; Fax: (internat.) +44-1223-336-033; E-mail: deposit@ccdc.cam.ac.uk].
  • 98
    • 0000841587 scopus 로고    scopus 로고
    • Calculation of these geometries with the B3LYP functional, irrespective of its inherent deficiency when it comes to localization of spin and/or charge (T. Bally, G. N. Sastry, J. Phys. Chem. A, 1997, 101, 7923-7925), has been justified, see ref. [2h, [8a]
    • (1997) J. Phys. Chem. A , vol.101 , pp. 7923-7925
    • Bally, T.1    Sastry, G.N.2
  • 99
    • 0242437461 scopus 로고    scopus 로고
    • The value 1.29 given in ref.[18a] needs to be corrected
    • The value 1.29 given in ref.[18a] needs to be corrected.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.