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Volumn 8, Issue 12, 2006, Pages 2647-2650

Pushing radical cyclization from regioselective to regiospecific: Cyclization of amidyl radicals controlled by vinylic halogen substitution

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Indexed keywords


EID: 33745533158     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol060983q     Document Type: Article
Times cited : (47)

References (28)
  • 1
    • 15044342910 scopus 로고
    • Katritzky, A. R., Ed.; Academic Press: New York
    • For reviews, see: (a) Esker, J.; Newcomb, M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: New York, 1993; Vol. 58, p 1.
    • (1993) Advances in Heterocyclic Chemistry , vol.58 , pp. 1
    • Esker, J.1    Newcomb, M.2
  • 3
    • 0001253023 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany
    • (c) Stella, L. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, p 407.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 407
    • Stella, L.1
  • 19
    • 33745530830 scopus 로고    scopus 로고
    • note
    • 2, rt) was identified to be 6-iodomethyl-2,3,4,5- tetrahydropyridine-2-one in 37% yield via a six-membered-ring closure, which in turn indicated that the formation of 9 was not an ionic process.
  • 20
    • 33745537905 scopus 로고    scopus 로고
    • note
    • The activation energies for 1,5-H migration of radicals 22 (R = Cl) and 23 (R = Cl) were also computed (B3LYP/6-31G*) to be 9.1 and 7.5 kcal/mol, respectively, much higher than the activation energies for the preferred cyclization, in excellent agreement with the experimental results in eqs 2 and 3.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.