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Volumn 8, Issue 23, 2006, Pages 5183-5186

Functionalized oxepines via fragmentation of highly strained epoxides

Author keywords

[No Author keywords available]

Indexed keywords

EPOXIDE;

EID: 33845258258     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol061682j     Document Type: Article
Times cited : (14)

References (37)
  • 24
    • 33845243875 scopus 로고    scopus 로고
    • note
    • These oxepine products decomposed slowly on untreated silica gel.
  • 27
    • 33845258888 scopus 로고    scopus 로고
    • note
    • 1H NMR coupling constants associated with the α-proton in oxepine 7 provided the relative stereochemical identity of the syn diastereomer. X-ray crystal analysis of the 3,5-dinitrobenzoyl ester of oxepine 8 provided the relative stereochemical identity of the anti diastereomer.
  • 28
    • 22244468979 scopus 로고    scopus 로고
    • see
    • For a computational comparison of the Cope rearrangement of divinyl oxirane and cyclopropane, see: (a) Zora, M. J. Org. Chem. 2005, 70, 6018.
    • (2005) J. Org. Chem. , vol.70 , pp. 6018
    • Zora, M.1
  • 36
    • 33845257260 scopus 로고    scopus 로고
    • note
    • Varian's NOESY1D (DPFGSE NOE) experiments for measurement of transient NOEs are generally lower in intensity than steady-state NOE values.
  • 37
    • 33845261750 scopus 로고    scopus 로고
    • note
    • In contrast to the systems with a methylene group, perhaps the epoxide oxygen allows for a more facile electrocyclic fragmentation of the C3-C4 bond in the C1-C2 retention pathway (Scheme 4).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.