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Volumn 569, Issue 1-2, 1998, Pages 3-14

N-bonded enolatorhenium(I) complexes having dimethylphenylphosphine ligands as active key intermediates in catalytic Knoevenagel and Michael reactions

Author keywords

Crystal structure; Knoevenagel reaction; Michael reaction; Rhenium dinitrogen complex; Rhenium enolate complex

Indexed keywords


EID: 0000787676     PISSN: 0022328X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0022-328X(98)00768-2     Document Type: Article
Times cited : (24)

References (31)
  • 21
    • 0007116617 scopus 로고
    • and references cited therein.
    • G.R. Desiraju, Acc. Chem. Res. 24 (1991) 290 and references cited therein.
    • (1991) Acc. Chem. Res. , vol.24 , pp. 290
    • Desiraju, G.R.1
  • 22
    • 0039203297 scopus 로고    scopus 로고
    • Note
    • -1 when 4 was isolated as blue precipitate by the addition of hexane into a blue THF solution.
  • 23
    • 0039203296 scopus 로고    scopus 로고
    • Note
    • We had observed that a reaction of 4 (23.4 mg, 0.0206 mmol) with tetracyanethylene (TCNE) (11.8 mg, 0.092 mmol) in THF solution (2 ml) resulted in the formation of ethyl (E)-2-cyano-3-phenylpropenoate (0.011 mmol, 52%), benzalomalononitrile (0.0012 mmol, 12%) and ethyl 2,3,3-tricyano-propenoate (0.0021 mmol, 10%). Although formation of 1,1-dicyano-2-phenylethylene and ethyl 2,3,3-tricyanopropenoate can be regarded as a formal olefin metathesis of TCNE with ethyl (E)-2-cyano-3-phenylpropenoate [17], this reaction actually proceeded in the absence of Re complexes. It is known that hydrolysis of TCNE gives malononitrile and dicyanoketone. Michael reaction of the generated malononitrile with ethyl (E)-2-cyano-3-phenylpropenoate followed by the elimination of ethyl cyanoacetate gives 1,1-dicyano-2-phenylethylene. The resulting ethyl cyanoacetate successively reacts with TCNE to yield ethyl 2,3,3-tricyanopropenoate and malononitrile [18]. All these reactions were independently determined.
  • 26
    • 0003855565 scopus 로고
    • Quartz optical cell having 3-way stopcock was used for UV-Vis analyses. cf. (a) Wiley Interscience, New York
    • Quartz optical cell having 3-way stopcock was used for UV-Vis analyses. cf. (a) A. Yamamoto, Organotransition Metal Chemistry, Wiley Interscience, New York, 1986, pp. 169.
    • (1986) Organotransition Metal Chemistry , pp. 169
    • Yamamoto, A.1
  • 31
    • 0004150157 scopus 로고
    • (b) University of Göttingen, Germany
    • (b) G.M. Sheldrick, SHELXL93, University of Göttingen, Germany, 1993.
    • (1993) SHELXL93
    • Sheldrick, G.M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.