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Volumn 68, Issue 20, 2003, Pages 7700-7706

Cyclopropanation of vinylidenecyclopropanes. Synthesis of 1-(dihalomethylene)spiropentanes

Author keywords

[No Author keywords available]

Indexed keywords

CYCLOPROPANATION;

EID: 0141655020     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0301595     Document Type: Article
Times cited : (71)

References (119)
  • 62
    • 0141583943 scopus 로고    scopus 로고
    • note
    • We attempted the reactions in concentrations of diarylvinylidenecyclopropanes from 0.025 to 0.22 mol/L and changed equivalents of haloform from 2.5 to 100 equiv, but the yields did not change appreciably. Progress of the reaction was monitored by TLC, and the reaction was continued until the substrates disappeared.
  • 75
    • 0141695608 scopus 로고    scopus 로고
    • note
    • Creary et al. suggested that the two phenyl groups in an analogous methylenecyclopropane should allow the rearrangement to occur below room temperature. The methylenecyclopropane rearrangement of systems substituted with phenyl and methoxy groups occur readily at room temperature. See refs lm and 3q.
  • 76
    • 0141807085 scopus 로고    scopus 로고
    • note
    • The radical-stabilizing effect of the 2-naphthyl group and halogen atoms has been discussed in refs 11-n.
  • 77
    • 0141807084 scopus 로고
    • For synthesis and reactions of spiropentane derivatives: (a) Zelinsky, N. Chem. Ber. 1913, 46, 160-172.
    • (1913) Chem. Ber. , vol.46 , pp. 160-172
    • Zelinsky, N.1
  • 87
    • 33947338509 scopus 로고
    • For synthesis and reactions of methylenespiropentane derivatives, see: (a) Skattebøl, L. J. Org. Chem. 1966, 31, 2789-2794.
    • (1966) J. Org. Chem. , vol.31 , pp. 2789-2794
    • Skattebøl, L.1
  • 95
    • 0003339292 scopus 로고
    • (i) Fitjer, L. Chem. Ber. 1982, 115, 1035-1046.
    • (1982) Chem. Ber. , vol.115 , pp. 1035-1046
    • Fitjer, L.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.