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Volumn 126, Issue 51, 2004, Pages 16912-16929

Dissociation of carbanions from acyl iridium compounds: An experimental and computational investigation

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CARBONYLATION; DERIVATIVES; DISSOCIATION; HYDRIDES; STEREOCHEMISTRY;

EID: 11244249600     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja045859l     Document Type: Article
Times cited : (30)

References (83)
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  • 29
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    • See ref 1, p 372
    • See ref 1, p 372.
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    • note
    • For related experiments, see ref 27 and references therein.
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    • note
    • A significant solvent effect on the rate of elimination is not expected upon substituting toluene for benzene.
  • 47
    • 0001588825 scopus 로고
    • For some early examples on the mechanism and stereochemistry of aldehyde and acid chloride decarbonylation, see: (a) Walborsky, H. M.; Allen, L. E. J. Am. Chem. Soc. 1971, 93, 5465-5468. (b) Stille, J. K.; Fries, R. W. J. Am. Chem. Soc. 1974, 96, 1514-1518. (c) Lau, K. S. Y.; Becker, Y.; Huang, F.; Baenziger, N.; Stille, J. K. J. Am. Chem. Soc. 1977, 99, 5664-5672.
    • (1971) J. Am. Chem. Soc. , vol.93 , pp. 5465-5468
    • Walborsky, H.M.1    Allen, L.E.2
  • 48
    • 11244330846 scopus 로고
    • For some early examples on the mechanism and stereochemistry of aldehyde and acid chloride decarbonylation, see: (a) Walborsky, H. M.; Allen, L. E. J. Am. Chem. Soc. 1971, 93, 5465-5468. (b) Stille, J. K.; Fries, R. W. J. Am. Chem. Soc. 1974, 96, 1514-1518. (c) Lau, K. S. Y.; Becker, Y.; Huang, F.; Baenziger, N.; Stille, J. K. J. Am. Chem. Soc. 1977, 99, 5664-5672.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 1514-1518
    • Stille, J.K.1    Fries, R.W.2
  • 49
    • 0141893877 scopus 로고
    • For some early examples on the mechanism and stereochemistry of aldehyde and acid chloride decarbonylation, see: (a) Walborsky, H. M.; Allen, L. E. J. Am. Chem. Soc. 1971, 93, 5465-5468. (b) Stille, J. K.; Fries, R. W. J. Am. Chem. Soc. 1974, 96, 1514-1518. (c) Lau, K. S. Y.; Becker, Y.; Huang, F.; Baenziger, N.; Stille, J. K. J. Am. Chem. Soc. 1977, 99, 5664-5672.
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 5664-5672
    • Lau, K.S.Y.1    Becker, Y.2    Huang, F.3    Baenziger, N.4    Stille, J.K.5
  • 50
    • 11244330110 scopus 로고    scopus 로고
    • note
    • Monitoring the reaction after 70 h indicated no further changes in product ratios.
  • 51
    • 11244271054 scopus 로고    scopus 로고
    • note
    • The solubility of the ammonium chloride salt in acetonitrile accounts for the presence of the protonate iridium carbonyl 21.
  • 52
    • 11244311177 scopus 로고    scopus 로고
    • note
    • 6 and gave rise to more alkene 34.
  • 57
    • 11244298277 scopus 로고    scopus 로고
    • note
    • Isolated crystals of thioether 35 showed no optical rotation, and analysis by chiral HPLC revealed that 35 consisted of a 1:1 ratio of enantiomers. Chiral HPLC of the crude reaction mixture containing 35 showed that the product was nearly racemic (9% ee).
  • 75
    • 11244330112 scopus 로고    scopus 로고
    • note
    • Higher sample concentrations did not affect the observed rates of reactions.
  • 79
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    • Schrödinger LLC: Portland, OR
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.