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Volumn 9, Issue 20, 2011, Pages 7057-7061

Claisen rearrangements of equilibrating allylic azides

Author keywords

[No Author keywords available]

Indexed keywords

ALLYLIC ALCOHOL; BASIC CONDITIONS; CLAISEN REARRANGEMENT; DIASTEREO-SELECTIVITY; REARRANGEMENT REACTIONS;

EID: 80053339235     PISSN: 14770520     EISSN: None     Source Type: Journal    
DOI: 10.1039/c1ob05972f     Document Type: Article
Times cited : (30)

References (51)
  • 5
    • 0030834193 scopus 로고    scopus 로고
    • For an example of rearrangement via an ionic transition state see
    • A. Padwa M. M. Sá Tetrahedron Lett. 1997 38 5087
    • (1997) Tetrahedron Lett. , vol.38 , pp. 5087
    • Padwa, A.1    Sá, M.M.2
  • 18
    • 3943111554 scopus 로고    scopus 로고
    • The syn product is typically formed when the ketene acetal bears a heteroatom-containing stereocentre at the 6′ position
    • B. Schmidt Synlett 2004 1541
    • (2004) Synlett , pp. 1541
    • Schmidt, B.1
  • 39
    • 0001823917 scopus 로고
    • By comparison of magnetic anisotropies
    • C. W. Bird Tetrahedron 1986 42 89
    • (1986) Tetrahedron , vol.42 , pp. 89
    • Bird, C.W.1
  • 41
    • 0000815416 scopus 로고
    • To exclude the effects of neutralisation of the propionic acid catalyst by the 2-pyridyl substituent, the reaction was repeated using 1.2 equivalents of propionic acid: the yield was unaffected
    • A. R. Katritzky M. Karelson N. Malhorta Heterocycles 1991 32 127
    • (1991) Heterocycles , vol.32 , pp. 127
    • Katritzky, A.R.1    Karelson, M.2    Malhorta, N.3
  • 45
    • 70349784871 scopus 로고    scopus 로고
    • The Cambridge X-ray structure database contains examples of azide internal nitrogen⋯H-O (alcohol) distances of less than 2.50 Å; see
    • B. Braida V. Prana P. C. Hiberty Angew. Chem., Int. Ed. 2009 48 5724
    • (2009) Angew. Chem., Int. Ed. , vol.48 , pp. 5724
    • Braida, B.1    Prana, V.2    Hiberty, P.C.3
  • 49
    • 34249322373 scopus 로고    scopus 로고
    • Other workers have postulated the existence of a hydrogen bonding interaction between azide and alcohol groups. 2,6a Azide thermolysis could be a significant competing pathway
    • R. Łysek S. Favre P. Vogel Tetrahedron 2007 63 6558
    • (2007) Tetrahedron , vol.63 , pp. 6558
    • Łysek, R.1    Favre, S.2    Vogel, P.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.