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Volumn , Issue 12, 1999, Pages 2761-2767

A new reaction between E-cinnamaldehyde and phenyllithium. Mechanistic studies

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EID: 0002620812     PISSN: 03009580     EISSN: None     Source Type: Journal    
DOI: 10.1039/a904635f     Document Type: Article
Times cited : (8)

References (66)
  • 2
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    • Carbonylation of main-group organometallic compounds
    • ed. S. Patai and Z. Rappoport, Wiley, Chichester, ch. 13, and references therein
    • N. S. Nudelman, Carbonylation of Main-Group Organometallic Compounds, in The Chemistry of Double Bonded Functional Groups, ed. S. Patai and Z. Rappoport, Wiley, Chichester, 1989, ch. 13, and references therein.
    • (1989) The Chemistry of Double Bonded Functional Groups
    • Nudelman, N.S.1
  • 18
    • 0042480243 scopus 로고    scopus 로고
    • note
    • The PM3 method was also used, but the results correlate better with the MNDO calculations.
  • 24
    • 0041979542 scopus 로고    scopus 로고
    • MOPAC 97 Fujitsu Limited, Cambridge Soft Corporation, 875 Massachusetts Avenue, Cambridge, MA 02139, USA
    • MOPAC 97 Fujitsu Limited, Cambridge Soft Corporation, 875 Massachusetts Avenue, Cambridge, MA 02139, USA.
  • 25
    • 0002382496 scopus 로고
    • Lithium parameters for MNDO: taken from MNDOC by W. Thiel, QCPE, 1982, 438, vol. 2, p. 63.
    • (1982) QCPE , vol.2-438 , pp. 63
    • Thiel, W.1
  • 42
    • 0042981179 scopus 로고    scopus 로고
    • note
    • The reactions were carried out in more concentrated solutions, [PhLi] = [1] = 0.2 M, and under these conditions the existence of 5 can be appreciated.
  • 49
    • 0042480237 scopus 로고    scopus 로고
    • note
    • We carried out the semiempirical studies with MNDO and PM3. Both methods gave us similar geometrical results but dissimilar relative energies. The previous successful use of MNDO for calculations of very closely related structures (cinnamyl and aryl derivatives, see references 16(b) and (c)) led us to take the decision to present only the MNDO results.
  • 50
    • 84961980743 scopus 로고
    • COSMO (conductor-like screening model) evaluates the solvent screening energy for a cavity based on the solvent-accessible surfaces and for a charge distribution derived from a distributed multipole analysis: A. Klamt and G. Schüürmann, J. Chem. Soc., Perkin Trans. 2, 1993, 799.
    • (1993) J. Chem. Soc., Perkin Trans. , vol.2 , pp. 799
    • Klamt, A.1    Schüürmann, G.2
  • 51
    • 0041478429 scopus 로고    scopus 로고
    • note
    • The calculated alternative pathways were: (a) attack of monomeric PhLi and similar rearrangement with a [1,2]-hydride shift; (b) previous deaggregation of dimer PhLi and attack followed by the [1,2]-hydride rearrangement; (c) addition of PhLi followed by attack of a second lithium with [1,2]-hydride shift and (d) attack of dimer PhLi with H shift from the carbonyl C to O. Options (a) and (b) seem attractive but the energetic changes in these options were unfavorable.
  • 53
    • 33947294592 scopus 로고
    • 3 arrangement, with the lithium atom coordinately bonded to the benzylic C, C ipso and C ortho, is also observed in the X-ray structure of benzyllithium, in S. P. Patterman, I. L. Karle and G. D. Stucky, J. Am. Chem. Soc., 1970, 92, 1150.
    • (1970) J. Am. Chem. Soc. , vol.92 , pp. 1150
    • Patterman, S.P.1    Karle, I.L.2    Stucky, G.D.3
  • 54
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    • note
    • We thank one of the referees for this comment.
  • 55
    • 0003467672 scopus 로고
    • Wiley-Interscience, New York, ch. 18
    • th edn., Wiley-Interscience, New York, 1992, ch. 18.
    • (1992) th Edn.
    • March, J.1
  • 59
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    • Other "dielectric continuum" models are: (a) G. P. Ford and B. Wang, J. Am. Chem. Soc., 1992, 114, 10563;
    • (1992) J. Am. Chem. Soc. , vol.114 , pp. 10563
    • Ford, G.P.1    Wang, B.2
  • 64
    • 0042981176 scopus 로고    scopus 로고
    • note
    • The reaction of 2 equivalents of PhLi with 2, at 20 °C in THF gives only 79% of 5 and 21% of 4.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.