Reaction of vinylcarbenoids with aldehydes: Formation of vinylcarbonyl ylides followed by ring closure to oxiranes and dihydrofurans

Tetrahedron Letters

Volumn 41, Issue 9, 2000, Pages 1457-1460

  Hamaguchi, Masashi ^a   Matsubara, Hiroshi ^a   Nagai, Toshikazu ^a  

^a OSAKA UNIVERSITY   (Japan)

Author keywords

Carbenes and carbenoids; Carbonyl ylides; Cyclization; Diazo compounds

Indexed keywords

ALDEHYDE DERIVATIVE; CARBENE; CARBENOID; ETHYLENE OXIDE DERIVATIVE; FURAN DERIVATIVE;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; REACTION ANALYSIS; SYNTHESIS;

EID: 0034716535     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02317-5     Document Type: Article

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13. 3) data for the compound 3d: δ 8.22 (d, J=8.9 Hz, 2H), 7.57 (d, J=8.9 Hz, 2H), 7.55-7.51 (m, 2H), 7.50-7.42 (m, 3H), 7.34 (d, J=8.9 Hz, 2H), 7.30 (d, J=8.9 Hz, 2H), 6.84 (s, 1H), 4.45 (s, 1H). Compound 4d: δ 8.04 (d, J=8.9 Hz, 2H), 7.56 (d, J=8.9 Hz, 2H), 7.43 (d, J=8.6 Hz, 2H), 7.41 (d, J=8.6 Hz, 2H), 7.36-7.33 (m, 2H), 7.25-7.23 (m, 3H), 7.13 (s, 1H), 4.84 (s, 1H). Compound 5d: δ 8.04 (d, J=8.6 Hz, 2H), 7.78-7.75 (m, 2H), 7.52-7.48 (m, 3H), 7.35 (d, J=8.6 Hz, 2H), 7.12 (d, J=8.9 Hz, 2H), 7.07 (d, J=8.9 Hz, 2H), 6.30 (s, 1H), 5.74 (s, 1H). Compound 6d: δ 8.30 (d, J=8.9 Hz, 2H), 7.76-7.72 (m, 2H), 7.51-7.47 (m, 9H), 5.65 (s, 1H), 5.62 (s, 1H).
14. 1H NMR spectra of the reaction mixtures.
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