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Volumn 69, Issue 17, 2004, Pages 5763-5765

Facile synthesis of oxabicyclic alkenes by ultrasonication-promoted diels-alder cycloaddition of furano dienes (Journal of Organic Chemistry (2004) 69, (5763) DOI: 10.1021/jo049210a);Facile synthesis of oxabicyclic alkenes by ultrasonication-promoted Diels-Alder cycloaddition of furano Dienes

Author keywords

[No Author keywords available]

Indexed keywords

SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); ULTRASONIC APPLICATIONS;

EID: 4043101688     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9020002     Document Type: Erratum
Times cited : (26)

References (50)
  • 8
    • 0003075009 scopus 로고    scopus 로고
    • For an excellent review (Using Ring-Opening Reactions of Oxabicyclic Compounds as a Strategy in Organic Synthesis), see: (a) Chiu, P.; Lautens, M. Top. Curr. Chem. 1997, 190, 1-85.
    • (1997) Top. Curr. Chem. , vol.190 , pp. 1-85
    • Chiu, P.1    Lautens, M.2
  • 27
    • 0004091137 scopus 로고    scopus 로고
    • Luche, J.-L., Ed.; Plenum Press, New York; Chapter 3
    • (e) Fillion, H.; Luche, J.-L. In Synthetic Organic Sonochemistry; Luche, J.-L., Ed.; Plenum Press: 1998, New York; Chapter 3, pp 91-106.
    • (1998) Synthetic Organic Sonochemistry , pp. 91-106
    • Fillion, H.1    Luche, J.-L.2
  • 36
    • 0242642973 scopus 로고
    • For a formal [3 + 4] cycloaddition of furan, see: (i) Joshi, N. N.; Hoffmann, H. M. R. Tetrahedron Lett. 1986, 27, 687. For an example on dramatic improvement of Diels-Alder reaction in water under ultrasonication, see:
    • (1986) Tetrahedron Lett. , vol.27 , pp. 687
    • Joshi, N.N.1    Hoffmann, H.M.R.2
  • 39
    • 4043152268 scopus 로고    scopus 로고
    • note
    • Cycloaddition product was severely contaminated with aromatized and other polymeric byproducts under these forcing conditions.
  • 40
    • 4043065886 scopus 로고    scopus 로고
    • note
    • Thermal conditions (at 80 °C) did not result in a better yield of cycloaddition product 6 but instead led to more side reactions, presumably due to the faster retro-Diels-Alder process of 6; cf. ref 14a.
  • 43
    • 0011278930 scopus 로고
    • For an earlier study, see also: (c) Herz, W. J. Am. Chem. Soc. 1946, 68, 2732.
    • (1946) J. Am. Chem. Soc. , vol.68 , pp. 2732
    • Herz, W.1
  • 44
    • 4043126936 scopus 로고    scopus 로고
    • note
    • Cis substituent of 2-vinylic furan 4 may further (sterically) prevent the access of exo-cyclic diene towards dienophile.
  • 49
    • 4043104288 scopus 로고    scopus 로고
    • note
    • Unreacted furano derivatives can be easily recovered in good yield.
  • 50
    • 4043182135 scopus 로고    scopus 로고
    • note
    • For General Experimental Procedures, cf. Supporting Information of ref 4c.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.