Synthesis of functionalized phenolic derivatives via the benzannulation of dienylketenes formed by a thermal Wolff rearrangement of α-diazo-β-keto compounds

Tetrahedron

Volumn 52, Issue 19, 1996, Pages 6665-6684

  Collomb, Didier ^a   Deshayes, Christian ^a   Doutheau, Alain ^a  

^a UNIVERSITÉ DE LYON   (France)

Author keywords

[No Author keywords available]

Indexed keywords

PHENOL DERIVATIVE; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0029932465     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00318-3     Document Type: Article

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41. The configuration of the α,β carbon-carbon double bond in compounds 2a-d was established by the chemical shift of the β-proton: 5.96-6.10 ppm for the cis isomer and 6.88-7.00 for the trans isomer (see ref. 12a). The cis configuration of compound 2e was established by the chemical shifts of its aromatic protons (7.12-7.36) which appeared similar to those of 2a-«s (7.15-7.38) and different from those of 2a-trans (7.25-7.41 and 7.69-7.77). The configuration of 2g-trans was established on the basis of the chemical shift.of its vinylic proton.
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58. 1H-NMR spectra of crude products. When compounds 3 and 4 were prepared from a mixture of steroisomers of compounds 2, we observed no significative modification in this ratio, excepted for 4h after purification (see text).
59. Caution! This compound is potentially explosive.