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Volumn 28, Issue 5, 2004, Pages 570-577

Persistent radical effect in the intramolecular addition of benzylic radicals onto ketenimines: Selective cross-coupling of α-(indol-2-yl)- benzyl radicals with the 1-cyano-1-methylethyl radical

Author keywords

[No Author keywords available]

Indexed keywords

2,2' AZOBISISOBUTYRONITRILE; BENZYL DERIVATIVE; BENZYLPHENYLSELENIDE; BUTYRONITRILE; DIMETHYL 2',2' AZOBISISOBUTYRATE; INDOLE; ISOBUTYRIC ACID DERIVATIVE; KETENE DERIVATIVE; METHYL GROUP; PROPIONIC ACID DERIVATIVE; PROPIONITRILE; SELENIDE; SILANE DERIVATIVE; TRIS(TRIMETHYLSILYL)SILANE; UNCLASSIFIED DRUG;

EID: 2942715432     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/b312930f     Document Type: Article
Times cited : (30)

References (46)
  • 1
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    • Griller, D.1    Ingold, K.U.2
  • 2
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    • (a) For a seminal paper in which the PRE was recognized see: H. Fischer, J. Am. Chem. Soc., 1986, 108, 3925-3927;
    • (1986) J. Am. Chem. Soc. , vol.108 , pp. 3925-3927
    • Fischer, H.1
  • 3
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    • (b) for the naming of the principle of PRE see: B. E. Daikh and R. G. Finke, J. Am. Chem. Soc., 1992, 114, 2938-2943;
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 2938-2943
    • Daikh, B.E.1    Finke, R.G.2
  • 4
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    • (c) for an excellent review on the PRE see: H. Fischer, Chem. Rev., 2001, 101, 3581-3610.
    • (2001) Chem. Rev. , vol.101 , pp. 3581-3610
    • Fischer, H.1
  • 7
    • 0035896265 scopus 로고    scopus 로고
    • For a selection of PRE in organic synthesis see: (c) A. Studer, Chem. Eur. J., 2001, 7, 1159-1164; (d) A. D. Allen, M. F. Fenwick, H. H. Riyad and T. T. Tidwell, J. Org. Chem., 2001, 66, 5759-5765; (e) C. Leroi, B. Fenet, J.-L. Couturier, O. Guerret and M. A. Ciufolini, Org. Lett., 2003, 5, 1079-1081.
    • (2001) Chem. Eur. J. , vol.7 , pp. 1159-1164
    • Studer, A.1
  • 8
    • 0035943267 scopus 로고    scopus 로고
    • For a selection of PRE in organic synthesis see: (c) A. Studer, Chem. Eur. J., 2001, 7, 1159-1164; (d) A. D. Allen, M. F. Fenwick, H. H. Riyad and T. T. Tidwell, J. Org. Chem., 2001, 66, 5759-5765; (e) C. Leroi, B. Fenet, J.-L. Couturier, O. Guerret and M. A. Ciufolini, Org. Lett., 2003, 5, 1079-1081.
    • (2001) J. Org. Chem. , vol.66 , pp. 5759-5765
    • Allen, A.D.1    Fenwick, M.F.2    Riyad, H.H.3    Tidwell, T.T.4
  • 9
    • 0141742136 scopus 로고    scopus 로고
    • For a selection of PRE in organic synthesis see: (c) A. Studer, Chem. Eur. J., 2001, 7, 1159-1164; (d) A. D. Allen, M. F. Fenwick, H. H. Riyad and T. T. Tidwell, J. Org. Chem., 2001, 66, 5759-5765; (e) C. Leroi, B. Fenet, J.-L. Couturier, O. Guerret and M. A. Ciufolini, Org. Lett., 2003, 5, 1079-1081.
    • (2003) Org. Lett. , vol.5 , pp. 1079-1081
    • Leroi, C.1    Fenet, B.2    Couturier, J.-L.3    Guerret, O.4    Ciufolini, M.A.5
  • 11
    • 2942709436 scopus 로고    scopus 로고
    • ed. P. Renaud and M. P. Sibi, Wiley-VCH, Weinheim
    • (b) M. Georges, Radicals in Organic Synthesis, ed. P. Renaud and M. P. Sibi, Wiley-VCH, Weinheim, 2001, vol. 1, p. 479;
    • (2001) Radicals in Organic Synthesis , vol.1 , pp. 479
    • Georges, M.1
  • 17
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    • ed. P. Renaud and M. P. Sibi, Wiley-VCH, Weinheim
    • (a) S. Z. Zard, Radicals in Organic Synthesis, ed. P. Renaud and M. P. Sibi, Wiley-VCH, Weinheim, 2001, vol. 1, p. 90;
    • (2001) Radicals in Organic Synthesis , vol.1 , pp. 90
    • Zard, S.Z.1
  • 34
    • 2942751784 scopus 로고    scopus 로고
    • note
    • The purification by column chromatography of the C-methyl-C-phenyl ketenimines 9e,f must be carried out using a short path of silica gel to avoid their decomposition.
  • 35
    • 2942701704 scopus 로고    scopus 로고
    • note
    • On the basis of our previous results (Scheme 1), we presumed that the transformations 9 → 10 would also require a stoichiometric amount of the radical initiator, AIBN.
  • 38
    • 2942746121 scopus 로고    scopus 로고
    • note
    • Wako Chemical GmbH, technical specifications.
  • 39
    • 2942716616 scopus 로고    scopus 로고
    • note
    • For analytical and spectroscopic data of 2-diphenylmethyl-7-methylindole 15 see ref. 5b. The conversion of ketenimine 9b into indole 15 is a reductive process in which the hydrogen atom donor toward the intermediate radical 13b is not obvious. A similar result was found and discussed in ref. 5b.


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