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Volumn 72, Issue 3, 2007, Pages 898-911

Effect of chain length on radical to carbanion cyclo-coupling of bromoaryl alkyl-linked oxazolines: 1,3-Areneotropic migration of oxazolines

Author keywords

[No Author keywords available]

Indexed keywords

BROMOARYL ALKYL-LINKED OXAZOLINES; CARBANION CYCLO-COUPLING; DIASTEREOSELECTIVITY; PRECURSOR;

EID: 33846896938     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0620720     Document Type: Article
Times cited : (29)

References (49)
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    • Renaud, P, Sibi, S, Eds, Wiley-VCH: Weinheim
    • (e) In Radicals in Organic Synthesis; Renaud, P., Sibi, S., Eds.; Wiley-VCH: Weinheim, 2001.
    • (2001) Radicals in Organic Synthesis
  • 13
    • 0027968145 scopus 로고
    • and references therein
    • (a) Savéant, J.-M. Tetrahedron, 1994, 50, 10117-10165 and references therein.
    • (1994) Tetrahedron , vol.50 , pp. 10117-10165
    • Savéant, J.-M.1
  • 27
    • 33846908216 scopus 로고
    • Morrison, J. D, Ed, Academic Press: Orlando, Chapter 3
    • Lutomski, K. A.; Myers, A. I. In Asymmertic Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, 1984; Vol. 3, Chapter 3.
    • (1984) Asymmertic Synthesis , vol.3
    • Lutomski, K.A.1    Myers, A.I.2
  • 31
    • 0034704888 scopus 로고    scopus 로고
    • Faust, R.; Garrett, P. J.; Jones, R.; Yeh, L.-K.; Tsotinis, A.; Panoussopoulou, M.; Calogeropoulou, T.; The, M.-T.; Sugden, D. J. Med. Chem. 2000, 43, 1050-1061.
    • Faust, R.; Garrett, P. J.; Jones, R.; Yeh, L.-K.; Tsotinis, A.; Panoussopoulou, M.; Calogeropoulou, T.; The, M.-T.; Sugden, D. J. Med. Chem. 2000, 43, 1050-1061.
  • 36
    • 33846894878 scopus 로고    scopus 로고
    • In some experiments a fifth minor component, 2-(1,5-diphenylnonan-5-yl)4, 4-dimethyl-2-oxazoline, derived from reaction of an intermediate with excess butyl lithium (or degradation product there from) was also obtained
    • In some experiments a fifth minor component, 2-(1,5-diphenylnonan-5-yl)4, 4-dimethyl-2-oxazoline, derived from reaction of an intermediate with excess butyl lithium (or degradation product there from) was also obtained.
  • 39
    • 33846926056 scopus 로고    scopus 로고
    • 2-NH.
    • 2-NH.
  • 42
    • 33846929763 scopus 로고    scopus 로고
    • Frisch M. J. et al. Gaussian 03, Revision A.1; Gaussian Inc.: Pittsburgh, PA, 2003 (see Supporting Information for full citation).
    • Frisch M. J. et al. Gaussian 03, Revision A.1; Gaussian Inc.: Pittsburgh, PA, 2003 (see Supporting Information for full citation).
  • 45
    • 33846912147 scopus 로고    scopus 로고
    • Alternative mechanisms involving initial formation of arynes are possible but are less likely because the EPR evidence proves the participation by radical anions because of the sensitivity of the reactions to oxygen and UV radiation and because of literature precedents for analogous SRN 1 processes mediated by LDA see refs 7, 12, and 15
    • RN 1 processes mediated by LDA (see refs 7, 12, and 15).
  • 46
    • 33846939437 scopus 로고    scopus 로고
    • Alternatively, after the butylation step, debrominative lithiation of the aryl ring would lead to an aryllithium that could undergo nucleophilic attack at the C=N bond of the oxazoline.
    • Alternatively, after the butylation step, debrominative lithiation of the aryl ring would lead to an aryllithium that could undergo nucleophilic attack at the C=N bond of the oxazoline.
  • 49
    • 33846910379 scopus 로고    scopus 로고
    • Assignment of isomer A or B is arbitrary
    • Assignment of isomer A or B is arbitrary.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.