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Volumn 127, Issue 8, 2005, Pages 2709-2716

Generation and reaction of tungsten-containing carbonyl ylides: [3 + 2]-Cycloaddition reaction with electron-rich alkenes

Author keywords

[No Author keywords available]

Indexed keywords

ADDITION REACTIONS; AROMATIC HYDROCARBONS; CARBONYLATION; CATALYSIS; DERIVATIVES; KETONES; MIXTURES; MOLECULAR STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SUBSTRATES; TUNGSTEN;

EID: 14744267835     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja044194k     Document Type: Article
Times cited : (124)

References (88)
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    • and references therein
    • (c) Huang, Q.; Larock, R. C. J. Org. Chem. 2003, 68, 980 and references therein,
    • (2003) J. Org. Chem. , vol.68 , pp. 980
    • Huang, Q.1    Larock, R.C.2
  • 18
    • 0034628238 scopus 로고    scopus 로고
    • and references therein
    • (e) Nan, Y.; Miao, H.; Yang, Z. Org. Lett. 2000, 2, 297 and references therein.
    • (2000) Org. Lett. , vol.2 , pp. 297
    • Nan, Y.1    Miao, H.2    Yang, Z.3
  • 29
    • 4344590797 scopus 로고    scopus 로고
    • (e) For a mechanistic study of the reaction described in ref 8a,b, see: Straub, B. F. Chem. Commun. 2004, 1726.
    • (2004) Chem. Commun. , pp. 1726
    • Straub, B.F.1
  • 46
    • 0032755406 scopus 로고    scopus 로고
    • For a review of vinylidene complexes, see: (a) McDonald, F. E. Chem.-Eur. J. 1999, 5, 3103.
    • (1999) Chem.-Eur. J. , vol.5 , pp. 3103
    • McDonald, F.E.1
  • 51
    • 14744273567 scopus 로고    scopus 로고
    • note
    • See the Supporting Information.
  • 52
    • 0001266992 scopus 로고
    • Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford
    • For a review of π-complexes of group 6 metals, see: Whiteley, M. W. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds.; Pergamon: Oxford, 1995; Vol. 5, p 331.
    • (1995) Comprehensive Organometallic Chemistry II , vol.5 , pp. 331
    • Whiteley, M.W.1
  • 68
    • 14744271636 scopus 로고    scopus 로고
    • note
    • The same reaction of 1d with ketene acetal did not give the corresponding cycloadduct, but aldol-type products 9 and 10 were produced in 85% yield. (Diagram presented).
  • 72
    • 0042207133 scopus 로고
    • It is well-known that C-H insertion is facilitated by the electron donation from á-oxygen. For the electronic factor of carbene insertion into C-H bonds, see: (a) Seyferth, D.; Mai, V. A.; Gordon, M. E. J. Org. Chem. 1970, 35, 1993.
    • (1970) J. Org. Chem. , vol.35 , pp. 1993
    • Seyferth, D.1    Mai, V.A.2    Gordon, M.E.3
  • 74
    • 14744269118 scopus 로고    scopus 로고
    • note
    • The calculations were performed with Gaussian 03 using the B3LYP hybrid density functional method. The lanl2dz basis set was used for the W atom, and the 6-31G* basis sets were used for the other atoms.
  • 82
    • 14744276976 scopus 로고    scopus 로고
    • note
    • For the preparation of 1c, see the Supporting Information.
  • 86
    • 14744274161 scopus 로고    scopus 로고
    • note
    • For NMR charts, see the Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.