6533b822fe1ef96bd127ca87
RESEARCH PRODUCT
Ring transformation of furfural into an unusual bicyclic system: Characterisation and dynamic stereochemistry of 6,7-diethoxycarbonyl-6,7-diaza-8-oxabicyclo[3,2,1]oct-3-en-2-one
M. Eugenia González-rosendeDonal Peter O’learySuzanne TwomeyW. Brian JenningsJosé Sepúlveda-arquesElena Zaballos-garcíaJ. Miquel Jorda-gregorisubject
Bicyclic moleculeStereochemistryOrganic ChemistryCarbon-13 NMRFormyl groupFurfuralRing (chemistry)BiochemistryDiethyl azodicarboxylatechemistry.chemical_compoundchemistrySlow rotationDrug DiscoveryDynamic stereochemistrydescription
Abstract 2-Formylthiophene and 3-formylindole react with diethyl azodicarboxylate to give simple products derived from reactions on the formyl group whereas 2-formylfuran reacts to give the unexpected bicyclic title compound. 1 H and 13 C NMR studies indicate that this compound undergoes a series of three dynamic conformational changes over the temperature range 50 to −90°C which are ascribed to slow rotation about the exocyclic carbamate bonds and hindered bridge inversion.
| year | journal | country | edition | language |
|---|---|---|---|---|
| 1997-07-01 | Tetrahedron |