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Volumn 131, Issue 36, 2009, Pages 12910-12911

Allene synthesis via C-C fragmentation: Method and mechanistic insight

Author keywords

[No Author keywords available]

Indexed keywords

ALLENES; EXPERIMENTAL DATA; FUNCTIONALIZED; HIGH YIELD; STEREOSPECIFIC; TRIFLATES;

EID: 70349124215     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja906189h     Document Type: Article
Times cited : (52)

References (40)
  • 1
    • 24944584108 scopus 로고    scopus 로고
    • Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH Verlag: Weinhelm
    • Hashmi, A. S. K. In Modern Allene Chemistry, Vol.1; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH Verlag: Weinhelm, 2004; pp 3-36.
    • (2004) Modern Allene Chemistry , vol.1 , pp. 3-36
    • Hashmi, A.S.K.1
  • 2
    • 22944443399 scopus 로고    scopus 로고
    • Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH Verlag: Weinhelm
    • Ma, S. In Modern Allene Chemistry, Vol.2; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH Verlag: Weinhelm, 2004; pp 595-684.
    • (2004) Modern Allene Chemistry , vol.2 , pp. 595-684
    • Ma, S.1
  • 6
    • 15444364740 scopus 로고    scopus 로고
    • Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH Verlag: Weinhelm
    • (a) Krause, N.; Hoffmann-Roder, A. In Modern Allene Chemistry, Vol.2; Krause, N., Hashmi, A. S. K., Eds.; Wiley-VCH Verlag: Weinhelm, 2004; pp 997-1017.
    • (2004) Modern Allene Chemistry , vol.2 , pp. 997-1017
    • Krause, N.1    Hoffmann-Roder, A.2
  • 32
    • 70349099064 scopus 로고    scopus 로고
    • Triflate 15 was derived from enantioenriched Wieland-Miecher Ketone
    • Triflate 15 was derived from enantioenriched Wieland-Miecher Ketone.
  • 33
    • 70349160628 scopus 로고    scopus 로고
    • See Supporting Information for details
    • See Supporting Information for details.
  • 34
    • 70349119747 scopus 로고    scopus 로고
    • The immediate fragmentation products (not observed) are imines. Use of THF accelerated the isomerization process (1 h: 23:24 = 1:1, 85% yield, 85% conversion)
    • The immediate fragmentation products (not observed) are imines. Use of THF accelerated the isomerization process (1 h: 23:24 = 1:1, 85% yield, 85% conversion).
  • 35
    • 0038626673 scopus 로고    scopus 로고
    • revision C.02; Gaussian, Inc.: Wallingford, CT, Exchange potentials
    • (a) Frisch, M. J.; Gaussian 03, revision C.02; Gaussian, Inc.: Wallingford, CT, 2004. Exchange potentials:
    • (2004) Gaussian 03
    • Frisch, M.J.1
  • 36
    • 0000189651 scopus 로고
    • Correlation functional
    • (b) Becke, A. D. J. Chem. Phys. 1993, 98, 5648. Correlation functional:
    • (1993) J. Chem. Phys. , vol.98 , pp. 5648
    • Becke, A.D.1
  • 38
    • 33748591851 scopus 로고    scopus 로고
    • calc and experiment is likely due in part to the degree of separation that exists between the transition states and the product ground states
    • calc and experiment is likely due in part to the degree of separation that exists between the transition states and the product ground states.
    • (2006) Org. Lett. , vol.8 , pp. 3631
    • Wodrich, M.D.1    Corminboeuf, C.2    Schleyer, P.V.R.3
  • 39
    • 70349151197 scopus 로고    scopus 로고
    • Transition states for chlorine and fluorine substituted piperidines were calculated and compared with the bromine substituted TS I (see Supporting Information). The enthalpy of the reaction for the series was-F 13.5 kcal/ mol,-Cl 9.2 kcal/mol, and-Br 8.3 kcal/mol, consistent with leaving group ability
    • Transition states for chlorine and fluorine substituted piperidines were calculated and compared with the bromine substituted TS I (see Supporting Information). The enthalpy of the reaction for the series was-F 13.5 kcal/ mol,-Cl 9.2 kcal/mol, and-Br 8.3 kcal/mol, consistent with leaving group ability.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.