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Volumn 345, Issue 3, 2003, Pages 329-332

Microwave Heating Effects Rapid and Selective Decarboalkoxylation of Mono-Alkylated Malonates and β-Ketoesters

Author keywords

Acetoacetic ester synthesis; Decarboalkoxylation; Hydrolysis; Malonic ester synthesis; Microwave heating

Indexed keywords

ACID; CARBON; KETONE DERIVATIVE; MALONIC ACID DERIVATIVE; REAGENT; WATER;

EID: 0242522402     PISSN: 16154150     EISSN: None     Source Type: Journal    
DOI: 10.1002/adsc.200390033     Document Type: Article
Times cited : (26)

References (27)
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    • For reviews on microwave assisted organic synthesis, see: a) S. Caddick, Tetrahedron 1995, 51, 10403; b) C. R. Strauss, R. W. Trainor, Aust. J. Chem. 1995, 48, 1665; c) L. Perreux, A. Loupy, Tetrahedron 2001, 57, 9199; c) for practical and safety considerations regarding solvents, apparatus and methods, see: B. L. Hayes, Microwave Synthesis, CEM Publishing, Matthews, NC, 2002.
    • (1995) Tetrahedron , vol.51 , pp. 10403
    • Caddick, S.1
  • 9
    • 84924213784 scopus 로고
    • For reviews on microwave assisted organic synthesis, see: a) S. Caddick, Tetrahedron 1995, 51, 10403; b) C. R. Strauss, R. W. Trainor, Aust. J. Chem. 1995, 48, 1665; c) L. Perreux, A. Loupy, Tetrahedron 2001, 57, 9199; c) for practical and safety considerations regarding solvents, apparatus and methods, see: B. L. Hayes, Microwave Synthesis, CEM Publishing, Matthews, NC, 2002.
    • (1995) Aust. J. Chem. , vol.48 , pp. 1665
    • Strauss, C.R.1    Trainor, R.W.2
  • 10
    • 0035813242 scopus 로고    scopus 로고
    • For reviews on microwave assisted organic synthesis, see: a) S. Caddick, Tetrahedron 1995, 51, 10403; b) C. R. Strauss, R. W. Trainor, Aust. J. Chem. 1995, 48, 1665; c) L. Perreux, A. Loupy, Tetrahedron 2001, 57, 9199; c) for practical and safety considerations regarding solvents, apparatus and methods, see: B. L. Hayes, Microwave Synthesis, CEM Publishing, Matthews, NC, 2002.
    • (2001) Tetrahedron , vol.57 , pp. 9199
    • Perreux, L.1    Loupy, A.2
  • 11
    • 0141609874 scopus 로고    scopus 로고
    • CEM Publishing, Matthews, NC
    • For reviews on microwave assisted organic synthesis, see: a) S. Caddick, Tetrahedron 1995, 51, 10403; b) C. R. Strauss, R. W. Trainor, Aust. J. Chem. 1995, 48, 1665; c) L. Perreux, A. Loupy, Tetrahedron 2001, 57, 9199; c) for practical and safety considerations regarding solvents, apparatus and methods, see: B. L. Hayes, Microwave Synthesis, CEM Publishing, Matthews, NC, 2002.
    • (2002) Microwave Synthesis
    • Hayes, B.L.1
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    • 0242710472 scopus 로고    scopus 로고
    • M. S. Thesis, University of Pittsburgh
    • N. Fairweather, M. S. Thesis, University of Pittsburgh, 2002.
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    • Fairweather, N.1
  • 21
    • 0000281617 scopus 로고
    • For mechanistic studies on hydrolysis of β-ketoesters and malonate esters, see: a) A. P. Krapcho, J. F. Weimaster, J. M. Eldridge, E. G. E. Jahngen, Jr., A. J. Lovey, W. P. Stephens, J. Org. Chem. 1978, 43 138; b) B. Holmquist, T. C. Bruice, J. Am. Chem. Soc. 1969, 91, 2993.
    • (1969) J. Am. Chem. Soc. , vol.91 , pp. 2993
    • Holmquist, B.1    Bruice, T.C.2
  • 22
    • 33847804686 scopus 로고
    • The activation of thiol ester group by intramolecular hydrogen bonding was proposed for the Corey-Nicolaou lactonization: E. J. Corey, K. C. Nicolaou, J. Am. Chem. Soc. 1974, 96, 5614; intramolecular hydrogen bonding was also proposed to explain a highly selective reduction process: T. N. Salzmann, R. W. Ratcliffe, B. G. Christensen, F. A. Bouffard, J. Am. Chem. Soc. 1980, 102, 6163.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 5614
    • Corey, E.J.1    Nicolaou, K.C.2
  • 23
    • 0019168718 scopus 로고
    • The activation of thiol ester group by intramolecular hydrogen bonding was proposed for the Corey-Nicolaou lactonization: E. J. Corey, K. C. Nicolaou, J. Am. Chem. Soc. 1974, 96, 5614; intramolecular hydrogen bonding was also proposed to explain a highly selective reduction process: T. N. Salzmann, R. W. Ratcliffe, B. G. Christensen, F. A. Bouffard, J. Am. Chem. Soc. 1980, 102, 6163.
    • (1980) J. Am. Chem. Soc. , vol.102 , pp. 6163
    • Salzmann, T.N.1    Ratcliffe, R.W.2    Christensen, B.G.3    Bouffard, F.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.