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Volumn 68, Issue 19, 2003, Pages 7243-7248

Palladium-catalyzed carbocyclization of allene-diene derivatives. Exploring different nucleophiles

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; ORGANIC ACIDS; ORGANIC SOLVENTS; STEREOCHEMISTRY;

EID: 0141566551     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034412c     Document Type: Article
Times cited : (30)

References (37)
  • 21
    • 0141808476 scopus 로고    scopus 로고
    • note
    • In the previous paper we had tentatively assigned product 4a as the cis-fused [7,5] ring system. In this paper it is proven to be trans fused.
  • 22
    • 0141585364 scopus 로고    scopus 로고
    • note
    • a values close to acetic acid seem to be the best. However, benzyl alcohol contradicts this statement.
  • 23
    • 0141473760 scopus 로고    scopus 로고
    • note
    • 1H NMR revealed that 2j′ was formed simultaneously with 2j.
  • 25
    • 0141697077 scopus 로고    scopus 로고
    • note
    • Acetone was dried over molecular sieves.
  • 27
    • 0141473759 scopus 로고    scopus 로고
    • note
    • 2 in the presence of p-benzoquinone at ambient temperature. It was shown that the stereochemistry of the product was cis, indicating that the nucleophile had added externally on the (π-allyl)palladium intermediate (see also ref 7b). (diagram presented).
  • 28
    • 0141808475 scopus 로고    scopus 로고
    • note
    • 1H NMR spectroscopy.
  • 29
    • 0141808474 scopus 로고    scopus 로고
    • note
    • 4a,5 indicates that H-5 and H-4a are axial and trans to one another. (diagram presented).
  • 32
    • 0141808473 scopus 로고    scopus 로고
    • note
    • 16 and benzyl alcohol are two nucleophiles that do not have the ability to migrate and therefore support this mechanism pathway. Competition between migration versus external attack has been proven to be dependent on the conformation, as previously investigated.20


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.