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Volumn 12, Issue 9, 2010, Pages 1628-1633

Rhodium-catalysed isomerisation of allylic alcohols in water at ambient temperature

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EID: 77956383799     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/c004964f     Document Type: Article
Times cited : (66)

References (57)
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    • For reviews on isomerisation of allylic alcohols, see
    • For reviews on isomerisation of allylic alcohols, see: R. Uma C. Crévisy R. Grée Chem. Rev. 2003 103 27-51.
    • (2003) Chem. Rev. , vol.103 , pp. 27-51
    • Uma, R.1    Crévisy, C.2    Grée, R.3
  • 17
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    • For highly efficient recent examples using organic solvents, see
    • For highly efficient recent examples using organic solvents, see: R. Uma M. K. Davies C. Crévisy R. Grée Eur. J. Org. Chem. 2001 3141-3146.
    • (2001) Eur. J. Org. Chem. , pp. 3141-3146
    • Uma, R.1    Davies, M.K.2    Crévisy, C.3    Grée, R.4
  • 43
    • 57649243236 scopus 로고    scopus 로고
    • For formation of metal hydrides and hydroxides via oxidative addition of water, see
    • For formation of metal hydrides and hydroxides via oxidative addition of water, see: O. V. Ozerov Chem. Soc. Rev. 2009 38 83-88.
    • (2009) Chem. Soc. Rev. , vol.38 , pp. 83-88
    • Ozerov, O.V.1
  • 45
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    • Joó et al. observed formation of Ru-aqua and hydroxide species with a water soluble Ru–NHC complex
    • Joó et al. observed formation of Ru-aqua and hydroxide species with a water soluble Ru–NHC complex: P. Csabai F. Joó Organometallics 2004 23 5640-5643.
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    • Csabai, P.1    Joó, F.2
  • 46
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    • We attribute this partially to the poor solubility of the catalyst in THF
    • We attribute this partially to the poor solubility of the catalyst in THF.
  • 47
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    • −1, according to supplier
    • −1, according to supplier.
  • 48
    • 85032775651 scopus 로고    scopus 로고
    • TOF = mol product/mol Rh/time
    • TOF = mol product/mol Rh/time.
  • 52
    • 85032781013 scopus 로고    scopus 로고
    • 1 takes place at approximately the same rate as that of 5a
    • 1 takes place at approximately the same rate as that of 5a.
  • 53
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    • We have observed before that under certain reaction conditions, metal hydrides formed in situ react with the allylic alcohols via an insertion/β-hydride elimination sequence
    • We have observed before that under certain reaction conditions, metal hydrides formed in situ react with the allylic alcohols via an insertion/β-hydride elimination sequence: A. Bartoszewicz B. Martín-Matute Org. Lett. 2009 11 1749-1752.
    • (2009) Org. Lett. , vol.11 , pp. 1749-1752
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    • 3-oxo-allyl intermediates as proposed by Trost and Gimeno may be involved. See references 6a and 23
    • 3-oxo-allyl intermediates as proposed by Trost and Gimeno may be involved. See references 6a and 23.


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