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Volumn 70, Issue 24, 2005, Pages 10046-10056

Development of the scope of a Co-mediated O→C rearrangement reaction

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; COBALT COMPOUNDS; ETHERS; STEREOCHEMISTRY;

EID: 28044435841     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0517895     Document Type: Article
Times cited : (18)

References (28)
  • 2
    • 0000134381 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L. S., Eds.; Pergamon: Oxford
    • (b) Caffyn, A. J. M.; Nicholas, K. M. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Hegedus, L. S., Eds.; Pergamon: Oxford, 1995; Vol. 12, p 685.
    • (1995) Comprehensive Organometallic Chemistry II , vol.12 , pp. 685
    • Caffyn, A.J.M.1    Nicholas, K.M.2
  • 16
    • 28044437219 scopus 로고    scopus 로고
    • note
    • 1H NMR spectrum. The stereochemical assignments of complexes 12 and 13 were made by analogy.
  • 17
    • 33845280186 scopus 로고
    • The addition of Lewis acid to noncomplexed enol ether substrates did not result in rearrangement to the corresponding ketones. A mixture of recovered starting material and alkene isomerization products were obtained instead. Additionally, significant substrate conversions were only observed when > 1.0 equiv of diethylaluminium chloride was employed. Indeed, the Lewis acid character of dialkylaluminium chlorides has been found to be highly dependent on reaction stoichiometry: (a) Evans, D. A.; Chapman, K. T.; Bisaha, J. J. Am. Chem. Soc. 1988, 110, 1238.
    • (1988) J. Am. Chem. Soc. , vol.110 , pp. 1238
    • Evans, D.A.1    Chapman, K.T.2    Bisaha, J.3
  • 20
    • 28044435447 scopus 로고    scopus 로고
    • note
    • The identity of the major isomers of 18 and 19 was not elucidated.
  • 22
    • 27944511863 scopus 로고    scopus 로고
    • note
    • 22ONa 277.1568, found 277.1556.
  • 23
    • 28044431888 scopus 로고    scopus 로고
    • note
    • Surprisingly, the Wittig reaction was only successful for cyclohexanone derivatives and failed to provide enol ether products when ketones of other ring sizes were employed.
  • 28
    • 28044452719 scopus 로고    scopus 로고
    • note
    • The identity of the major isomer was not elucidated.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.