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Volumn 689, Issue 21, 2004, Pages 3379-3387

Coupling of propargylsilanes with Fischer carbene chromium complexes: A new synthesis of conjugated dienes

Author keywords

Alkynes; Carbene complexes; Chromium; Dienes; Silicon migration

Indexed keywords

ALKADIENE; CARBENE; CARBON; CHROMIUM DERIVATIVE; ETHER DERIVATIVE; SILANE DERIVATIVE; SILICON;

EID: 4644241208     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jorganchem.2004.07.051     Document Type: Article
Times cited : (12)

References (33)
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    • For preliminary reports of this reaction, see
    • For preliminary reports of this reaction, see: J.W. Herndon P.P. Patel J. Org. Chem. 61 1996 4500-4501
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    • For a recent review of this reaction, see
    • For a recent review of this reaction, see K.H. Dötz P. Tomuschat Chem. Soc. Rev. 28 1999 187-198
    • (1999) Chem. Soc. Rev. , vol.28 , pp. 187-198
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    • For a recent review of this reaction, see
    • For a recent review of this reaction, see J.W. Herndon Curr. Org. Chem. 7 2003 329-352
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    • Herndon, J.W.1
  • 6
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    • We are unaware of an example of a 1,7-silicon shift process, however the 1,5-silicon shift is known
    • We are unaware of an example of a 1,7-silicon shift process, however the 1,5-silicon shift is known. M. Stradiotto P. Hazendonk A.D. Bain M.A. Brook M.J. McGlinchey Organometallics 19 2000 590-601
    • (2000) Organometallics , vol.19 , pp. 590-601
    • Stradiotto, M.1    Hazendonk, P.2    Bain, A.D.3    Brook, M.A.4    McGlinchey, M.J.5
  • 9
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    • The first letter refers to the stereochemistry of the end ether. The second letter refers to the stereochemistry of the alkenylsilane
    • The first letter refers to the stereochemistry of the end ether. The second letter refers to the stereochemistry of the alkenylsilane.
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    • 0031013620 scopus 로고    scopus 로고
    • Similarly successful carbene-alkyne couplings have been reported for pentenyloxycarbene complexes
    • Similarly successful carbene-alkyne couplings have been reported for pentenyloxycarbene complexes. J.W. Herndon P.P. Patel Tetrahedron Lett. 38 1997 59-62
    • (1997) Tetrahedron Lett. , vol.38 , pp. 59-62
    • Herndon, J.W.1    Patel, P.P.2
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    • A similar failure in geometry optimization of this complex was previously documented. Successful optimization was only effected starting from a non-cis arrangement of methyl groups
    • A similar failure in geometry optimization of this complex was previously documented. Successful optimization was only effected starting from a non-cis arrangement of methyl groups X. Wang E. Weitz J. Phys. Chem. A 106 2002 11782-11790
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  • 19
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    • For a discussion of deviation of alkene-metal complexes from totally symmetrical coordination see
    • For a discussion of deviation of alkene-metal complexes from totally symmetrical coordination see O. Eisenstein R. Hoffmann J. Am. Chem. Soc. 103 1981 4308-4320
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 4308-4320
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    • This explanation is very similar to that used to explain retention of stereochemistry in reaction of alkenylsilanes with electrophiles
    • This explanation is very similar to that used to explain retention of stereochemistry in reaction of alkenylsilanes with electrophiles I. Fleming J. Dunogues R. Smithers Org. React. 37 1989 57-575
    • (1989) Org. React. , vol.37 , pp. 57-575
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  • 22
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    • The silica gel was slurried ina 99:1 hexane:triethylamine solution prior to packing the chromatography column
    • The silica gel was slurried ina 99:1 hexane:triethylamine solution prior to packing the chromatography column.
  • 32
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    • Note that conversion of a trimethylsilyl group to a hydrogen changes the E-Z designation of the non-enol ether double bond due to changes in Cahn-Ingold priority number
    • Note that conversion of a trimethylsilyl group to a hydrogen changes the E-Z designation of the non-enol ether double bond due to changes in Cahn-Ingold priority number.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.