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Volumn , Issue 4, 2006, Pages 609-614

Ceric(IV)-mediated reaction of methylenecyclopropanes in organic synthesis: A facile access to dihydrofurans and cyclobutanones

Author keywords

1,3 dicarbonyl compounds; Ammonium cerium(IV) nitrate; Cyclobutanone; Dihydrofuran; Methylenecyclopropanes

Indexed keywords

ADDITION REACTIONS; DERIVATIVES; FURAN RESINS; NITRATES; REACTION KINETICS; SYNTHESIS (CHEMICAL);

EID: 33644524412     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-926298     Document Type: Article
Times cited : (34)

References (77)
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    • For some of the most recent results from this group, see: (a) Huang, X.; Chen, W. L.; Zhou, H. W. Synlett 2004, 329.
    • (2004) Synlett , pp. 329
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  • 51
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    • note
    • 2 = 0.907; Final R indices [I > 2σ(I)] R1 = 0.0470, wR2 = 0.0913.
  • 52
    • 33644551730 scopus 로고    scopus 로고
    • note
    • 3CN, therefore the cosolvent THF is required.
  • 53
    • 33644525800 scopus 로고
    • The cyclopropylmethyl radical is stabilized by the substituents on MCP, which does not undergo a cyclopropyl ring-opening radical rearrangement. It is further oxidized by a second equivalent of CAN to give the more stable cyclopropylcarbinyl cation, see: (a) Bowry, V. W.; Lusztyk, J.; Ingold, K. U. Chem. Commun. 1990, 92.
    • (1990) Chem. Commun. , pp. 92
    • Bowry, V.W.1    Lusztyk, J.2    Ingold, K.U.3
  • 54
    • 9644273928 scopus 로고    scopus 로고
    • In addition some 3-exo-trig processes have been described recently: (b) Sakuma, D.; Togo, H. Synlett 2004, 2501.
    • (2004) Synlett , pp. 2501
    • Sakuma, D.1    Togo, H.2
  • 58
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    • Wiley: New York, and references cited therein
    • (b) March, J. Advanced Organic Chemistry, 4th ed.; Wiley: New York, 1992, 169; and references cited therein.
    • (1992) Advanced Organic Chemistry, 4th Ed. , pp. 169
    • March, J.1
  • 60
    • 0001024887 scopus 로고
    • (b) de Meijere has previously reported cycloadditions onto a unique olefin bicyclopropylidene in which the cyclobutanone was formed in the reaction between bicyclopropylidene and 4-phenyl-1,2,4-triazoline-3,5-dione (PTAD) in wet acetone, see: de Meijere, A.; Erden, I.; Weber, W.; Kaufmann, D. J. Org. Chem. 1988, 53, 152.
    • (1988) J. Org. Chem. , vol.53 , pp. 152
    • De Meijere, A.1    Erden, I.2    Weber, W.3    Kaufmann, D.4
  • 61
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    • note
    • 2O, 4:1).
  • 64
    • 18744398145 scopus 로고    scopus 로고
    • During the preparation of our manuscript, manganese(III)-mediated oxidative annulation of MCPs with 1,3-dicarbonyl compounds was reported, see: Huang, J. W.; Shi, M. J. Org. Chem. 2005, 70, 3859.
    • (2005) J. Org. Chem. , vol.70 , pp. 3859
    • Huang, J.W.1    Shi, M.2
  • 65
    • 0001646582 scopus 로고
    • Such cyclobutanones can be formed in the reactions between MCPs and peracetic acid or MCPBA. (a) Crandall, J. K.; Conover, W. W. J. Org. Chem. 1978, 43, 3533.
    • (1978) J. Org. Chem. , vol.43 , pp. 3533
    • Crandall, J.K.1    Conover, W.W.2
  • 77
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    • Substituted MCPs 1 are readily available by the reaction of aldehydes/ketones with 3-bromopropylphosphonium bromide. It should be noted that the aryl-substituted MCPs are stable at -15 °C. For the synthesis of MCPs, see: Utimoto, K.; Tamura, M.; Sisido, K. Tetrahedron 1973, 29, 1169.
    • (1973) Tetrahedron , vol.29 , pp. 1169
    • Utimoto, K.1    Tamura, M.2    Sisido, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.