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Volumn 71, Issue 2, 2006, Pages 557-561

Rate constants for anilidyl radical cyclization reactions

Author keywords

[No Author keywords available]

Indexed keywords

ELECTROPHORESIS; PHENOLS; PHOTOLYSIS; SUBSTITUTION REACTIONS; TEMPERATURE MEASUREMENT;

EID: 30744447707     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo051953o     Document Type: Article
Times cited : (23)

References (37)
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    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany
    • Suáarez, E. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, pp 440-454.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 440-454
    • Suáarez, E.1
  • 7
    • 0038317136 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany
    • Hartung, J. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, pp 427-439.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 427-439
    • Hartung, J.1
  • 9
    • 15044342910 scopus 로고
    • Katritzky, A. R., Ed.; Academic Press: San Diego, CA
    • Esker, J. L.; Newcomb, M. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press: San Diego, CA, 1993; Vol. 58, pp 1-45.
    • (1993) Advances in Heterocyclic Chemistry , vol.58 , pp. 1-45
    • Esker, J.L.1    Newcomb, M.2
  • 11
    • 0001253023 scopus 로고    scopus 로고
    • Renaud, P., Sibi M. P., Eds.; Wiley-VCH: Weinheim, Germany
    • Stella, L. In Radicals in Organic Synthesis; Renaud, P., Sibi M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 2, pp 407-426.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 407-426
    • Stella, L.1
  • 25
    • 30744472590 scopus 로고    scopus 로고
    • note
    • A referee of an early draft suggested that the diphenylethene moiety in 31 might be participating in an internal electron transfer reaction for this radical. Consistent with that conjecture, the relative rate constant for a 5-exo cyclization reaction versus the tin hydride trapping of a p-methoxy-substituted anilidyl radical lacking the diphenylethene moiety was smaller than that of the unsubstituted parent. If the rates of the tin hydride trapping of the two radicals are comparable, then the cyclization of the p-methoxy-substituted radical in that study was slower than the cyclization of the parent radical, as expected from the results in Figure 2.
  • 32
    • 0000782249 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany
    • Newcomb, M. In Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol. 1, pp 317-336.
    • (2001) Radicals in Organic Synthesis , vol.1 , pp. 317-336
    • Newcomb, M.1
  • 33
    • 30744442485 scopus 로고    scopus 로고
    • note
    • Photochemically initiated preparative reactions could be performed, but photochemically initiated kinetic studies were not possible. The phenylthiyl radical formed as a byproduct in the photolysis reaction will react with tin hydride to give highly reactive thiophenol.
  • 34
    • 30744442971 scopus 로고    scopus 로고
    • note
    • Cursory studies showed that a change in solvent from THF to hexane had at most a minor effect on the rate constants for the cyclization of radical 3a.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.