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Volumn 63, Issue 3, 1998, Pages 422-423

Rhodium-Catalyzed Insertion of Carbenoids into β C-H Bonds of Silacycloalkanes: A Facile and General Approach to Functionalized Silacycloalkanes

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EID: 0000703884     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971910a     Document Type: Article
Times cited : (32)

References (33)
  • 14
    • 26144443825 scopus 로고
    • For reviews on the Rh-catalyzed reactions of diazo compounds, see: (a) Doyle, M. P. Chem. Rev. 1986, 86, 319. (b) Ye, T.; Mckervey, A. Chem. Rev. 1994, 94, 1091. (c) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797.
    • (1986) Chem. Rev. , vol.86 , pp. 319
    • Doyle, M.P.1
  • 15
    • 0000709206 scopus 로고
    • For reviews on the Rh-catalyzed reactions of diazo compounds, see: (a) Doyle, M. P. Chem. Rev. 1986, 86, 319. (b) Ye, T.; Mckervey, A. Chem. Rev. 1994, 94, 1091. (c) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797.
    • (1994) Chem. Rev. , vol.94 , pp. 1091
    • Ye, T.1    Mckervey, A.2
  • 16
    • 33748811198 scopus 로고
    • For reviews on the Rh-catalyzed reactions of diazo compounds, see: (a) Doyle, M. P. Chem. Rev. 1986, 86, 319. (b) Ye, T.; Mckervey, A. Chem. Rev. 1994, 94, 1091. (c) Padwa, A.; Austin, D. J. Angew. Chem., Int. Ed. Engl. 1994, 33, 1797.
    • (1994) Angew. Chem., Int. Ed. Engl. , vol.33 , pp. 1797
    • Padwa, A.1    Austin, D.J.2
  • 17
    • 85034472963 scopus 로고    scopus 로고
    • note
    • 2Si: C, 61.63; H, 10.34. Found: C, 61.82; H, 10.44.
  • 18
    • 0040535406 scopus 로고
    • Silacycloalkanes used in this work except for disilacyclopentanes are commercially available. Disilacyclopentanes were prepared by the Na/K-promoted cyclization of 1,3-bis(chlorosilyl)propanes: Kumada, M.; Tamao, K.; Takubo, T.; Ishikawa, M. J. Organomet. Chem. 1967, 9, 43.
    • (1967) J. Organomet. Chem. , vol.9 , pp. 43
    • Kumada, M.1    Tamao, K.2    Takubo, T.3    Ishikawa, M.4
  • 23
    • 85034480360 scopus 로고    scopus 로고
    • note
    • In the absence of 1c, hexyltrimethylsilane reacted with tert-butyl diazoacetate under catalytic conditions to give the corresponding β C-H bond insertion product in 36% yield.
  • 24
    • 85034483054 scopus 로고    scopus 로고
    • note
    • Under the same reaction conditions, less strained silacycloalkanes such as 1b and 1c did not react with benzoyl chloride.
  • 27
    • 0012887591 scopus 로고
    • Carbene carbons of Rh carbene complexes are highly electrophilic: (a) Doyle, M. P. Acc. Chem. Res. 1986, 19, 348. (b) Doyle, M. P. Recl. Trav. Chem. Pays-Bas 1991, 110, 305.
    • (1986) Acc. Chem. Res. , vol.19 , pp. 348
    • Doyle, M.P.1
  • 28
    • 84987184968 scopus 로고
    • Carbene carbons of Rh carbene complexes are highly electrophilic: (a) Doyle, M. P. Acc. Chem. Res. 1986, 19, 348. (b) Doyle, M. P. Recl. Trav. Chem. Pays-Bas 1991, 110, 305.
    • (1991) Recl. Trav. Chem. Pays-Bas , vol.110 , pp. 305
    • Doyle, M.P.1
  • 33
    • 85034485577 scopus 로고    scopus 로고
    • note
    • 16


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