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Volumn , Issue 11, 1998, Pages 1167-1174

Highly selective synthesis of polyfunctionalized carbo- and heterocycles based on ring expansion of squaric acid derivatives

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EID: 0000937422     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-5893     Document Type: Article
Times cited : (33)

References (38)
  • 1
    • 0004142086 scopus 로고
    • Academic Press: New York
    • West, R. Oxocarbons; Academic Press: New York, 1980.
    • (1980) Oxocarbons
    • West, R.1
  • 9
  • 23
    • 26844442529 scopus 로고
    • Abramovitch, R. A. Ed.; Plenum Press: New York, Chapter 6
    • Burn, P.; Wägell, B. In Reactive Intermediate; Abramovitch, R. A. Ed.; Plenum Press: New York, 1983; Vol. 3, Chapter 6.
    • (1983) Reactive Intermediate , vol.3
    • Burn, P.1    Wägell, B.2
  • 25
    • 0001216647 scopus 로고
    • Trost, B. M. Ed.; Pergamon Press: Oxford, Chapters 4.2.2 and 4.2.3
    • Curran, D. P. In Comprehensive Organic Synthesis; Trost, B. M. Ed.; Pergamon Press: Oxford, 1991; Vol. 4, Chapters 4.2.2 and 4.2.3.
    • (1991) Comprehensive Organic Synthesis , vol.4
    • Curran, D.P.1
  • 29
    • 26844504708 scopus 로고    scopus 로고
    • note
    • This was supported by PM3 calculations using a radical intermediate generated from 4-hydroxy-4-ethynylcyclobutenone as a simplified model; the 5-endo cyclized radical was estimated to be 5.2 kcal/mol more advantageous than the 5-exo cyclized radical, with an energy difference of 4.5 kcal/mol in relative stability (see ref. 18).
  • 36
    • 26844460569 scopus 로고    scopus 로고
    • note
    • The starting diazo-cyclobutenone was prepared by adding the lithium enolate of diazoacetate to cyclobutenedione at -78 °C.


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