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Volumn 1, Issue 23, 2003, Pages 4282-4292

Intramolecular addition of benzylic radicals onto ketenimines. Synthesis of 2-alkylindoles

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; ATOMS; DIMERIZATION; FREE RADICAL REACTIONS; MOLECULAR PHYSICS; NITROGEN COMPOUNDS; SYNTHESIS (CHEMICAL);

EID: 0346780232     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/b310593h     Document Type: Article
Times cited : (46)

References (88)
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    • (2001) Radicals in Organic Synthesis , vol.1-2
  • 8
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    • For recent applications of radical chemistry to the synthesis of natural products see: (a) E. Bacqué, F. Pautrat and S. Z. Zard, Org. Lett., 2003, 5, 325-328
    • (2003) Org. Lett. , vol.5 , pp. 325-328
    • Bacqué, E.1    Pautrat, F.2    Zard, S.Z.3
  • 20
    • 0037419167 scopus 로고    scopus 로고
    • To our knowledge no examples of radical reactions involving carbodiimides have been reported. For an example of radical addition to isocyanates, see: P. L. Minin and J. C. Walton, J. Org. Chem., 2003, 68, 2960-2963.
    • (2003) J. Org. Chem. , vol.68 , pp. 2960-2963
    • Minin, P.L.1    Walton, J.C.2
  • 48
    • 37049073783 scopus 로고
    • For reviews on radical cyclizations leading to indoles, see: (a) G. W. Gribble, Contemp. Org. Synth., 1994, 1, 145-172
    • (1994) Contemp. Org. Synth. , vol.1 , pp. 145-172
    • Gribble, G.W.1
  • 50
    • 0000450508 scopus 로고
    • N-(4-Methylphenyl)-C,C-diphenyl ketenimine 1 is a known compound: (a) C. L. Stevens and J. C. French, J. Am. Chem. Soc., 1954, 76, 4398-4402
    • (1954) J. Am. Chem. Soc. , vol.76 , pp. 4398-4402
    • Stevens, C.L.1    French, J.C.2
  • 54
    • 0346872842 scopus 로고    scopus 로고
    • note
    • For examples of addition reactions of TEMPO to ketenes, see: reference 6.
  • 55
    • 0003123493 scopus 로고    scopus 로고
    • ed. P. Renaud and M. P. Silbi, Wiley-VCH, Weinheim
    • For reviews on the radical xanthate transfer reaction, see: (a) S. Z. Zard, reference 1g pp. 90-108
    • (2001) Radicals in Organic Synthesis , vol.1-2 , pp. 90-108
    • Zard, S.Z.1
  • 61
    • 0346242533 scopus 로고    scopus 로고
    • note
    • A small amount (10-17%) of the imidate resulting from the addition of methanol to the central carbon atom of the cumulence function in ketenimines 7c,d was also isolated in this reaction.
  • 62
    • 0142222363 scopus 로고
    • 2-Diphenylmethylindole 9a is a known compound: L. L. J. Dolby and P. D. Lord, J. Org. Chem., 1969, 34, 2988-2993.
    • (1969) J. Org. Chem. , vol.34 , pp. 2988-2993
    • Dolby, L.L.J.1    Lord, P.D.2
  • 63
    • 0346242531 scopus 로고    scopus 로고
    • note
    • This is the reason why this radical transformation requires a stoichiometric amount of the peroxide used as a radical initiator.
  • 68
    • 0029828028 scopus 로고    scopus 로고
    • For similar reactions in which cyclohexane acts as an effective hydrogen donors, see: (c) B. Quiclet-Sire and S. Z. Zard, J. Am. Chem. Soc., 1996, 118, 9190-9191.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 9190-9191
    • Quiclet-Sire, B.1    Zard, S.Z.2
  • 70
    • 0346872841 scopus 로고    scopus 로고
    • note
    • ortho-Xylene was used as the substituted toluene in order to insure that the decomposition temperature of t-butyl peroxide was reached.
  • 71
    • 0028086078 scopus 로고
    • For the generation of radicals from thioxocarbamates of thionocarbonates and tris(trimethylsilyl)silane/AIBN, see: (a) M. Oba and K. Nishiyama, Tetrahedron, 1994, 50, 10193-10200
    • (1994) Tetrahedron , vol.50 , pp. 10193-10200
    • Oba, M.1    Nishiyama, K.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.