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Volumn 131, Issue 43, 2009, Pages 15695-15704

Which one is preferred: Myers-Saito cyclization of ene-yne-allene or Garratt-Braverman cyclization of conjugated bisallenic sulfone? A theoretical and experimental study

Author keywords

[No Author keywords available]

Indexed keywords

BASIC CONDITIONS; CLEAVING AGENTS; COMPUTATIONAL TECHNIQUE; CYCLIZATION PATHWAYS; CYCLIZATIONS; DNA CLEAVAGE; ENE-YNE; EXPERIMENTAL STUDIES; INVERSE RELATIONS; MECHANISTIC STUDIES; RATE DETERMINING STEP; REACTION PATHWAYS; SELF-QUENCHING; THEORETICAL PREDICTION;

EID: 70350676806     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9023644     Document Type: Article
Times cited : (49)

References (76)
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    • Nicolaou, K.C.1    Smith, A.L.2
  • 55
    • 33846200053 scopus 로고    scopus 로고
    • Although in principle the ene-yne-allene can also undergo Schmittel cyclization (SC) to form the fulvene diradical, we did not consider such a process in our theoretical calculations. Our chosen system is most likely to refrain from undergoing such a process, as Schmittel and co-workers have shown that only ene-yne-allenes with an aryl, silyl, or tert-butyl group attached to the alkyne terminus undergo SC. See: (a)
    • Although in principle the ene-yne-allene can also undergo Schmittel cyclization (SC) to form the fulvene diradical, we did not consider such a process in our theoretical calculations. Our chosen system is most likely to refrain from undergoing such a process, as Schmittel and co-workers have shown that only ene-yne-allenes with an aryl, silyl, or tert-butyl group attached to the alkyne terminus undergo SC. See: (a) Schmittel, M.; Strittmatter, M.; Mahajan, A. A.; Vavilala, C.; Cinar, M. E.; Maywald, M. ARKIVOC 2007, 2007 (viii), 66.
    • (2007) ARKIVOC 2007 , Issue.8 , pp. 66
    • Schmittel, M.1    Strittmatter, M.2    Mahajan, A.A.3    Vavilala, C.4    Cinar, M.E.5    Maywald, M.6
  • 61
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    • Frisch, M.J.1
  • 70
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    • note
    • The crystal structure has been deposited at the Cambridge Crystallographic Data Centre and has been allocated the deposition number CCDC 722767.
  • 72
    • 70350634371 scopus 로고    scopus 로고
    • note
    • Sulfone 4 and sulfoxide 17 can inflict DNA cleavage even at a concentration of 50 μM (the gel picture is included in the Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.