Unexpected formation of tetrasubstituted 2,3-dihydrofurans from the reactions of β-keto polyfluoroalkanesulfones with aldehydes

Journal of Organic Chemistry

Volumn 69, Issue 19, 2004, Pages 6486-6488

  Xing, Chunhui ^a   Zhu, Shizheng ^a  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; AROMATIC COMPOUNDS; CATALYSIS; CONDENSATION; FLUORINE CONTAINING POLYMERS; STEREOCHEMISTRY; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

KNOEVENAGEL CONDENSATION PRODUCTS; STEREOSELECTIVITY; TETRASUBSTITUTED 2,3-DIHYDROFURANS;

KETONES;

2,3 DIHYDROFURAN DERIVATIVE; ALDEHYDE DERIVATIVE; ALKANE DERIVATIVE; AROMATIC COMPOUND; BETA KETOPOLYFLUOROALKANESULFONE DERIVATIVE; FLUORINE DERIVATIVE; FURAN DERIVATIVE; PIPERIDINE; SULFONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGEN BOND; KNOEVENAGEL CONDENSATION; OXIDATION; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; REPRODUCIBILITY; STEREOCHEMISTRY; SUBSTITUTION REACTION; SYNTHESIS; TECHNIQUE; X RAY DIFFRACTION;

EID: 4644277618     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo049317y     Document Type: Article

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25. int = 0.0357), no observation [I > 2σ(I)] 4004, parameters 372.
26. The bond length of C23-C24 is 1.363 Å, which shows the double-bonded character; the bond length of C25-C26 is 1.556 Å.
27. 3): 4ad δ 8.08 (1H, s), 7.95 (2H, d, J = 7.5 Hz), 7.27-7.62 (5H, m), 7.11 (2H, d, J = 8.1 Hz), 2.32 (3H, s); 4ae δ 8.04 (1H, s), 7.96 (2H, d, J = 7.2 Hz), 7.36-7.59 (5H, m), 6.79 (2H, d, J = 8.7 Hz), 3.77 (3H, s). Other spectral data will be reported in detail. Manuscript in preparation.