Journal of the Mexican Chemical Society
versión impresa ISSN 1870-249X
JANKOWSKI, C. K. et al. Reactions of Vinylcyclopropane and Bicyclopropyl Compounds With Maleic Anhydride. J. Mex. Chem. Soc [online]. 2009, vol.53, n.4, pp. 220-228. ISSN 1870-249X.
Vinylcyclopropane and bicyclopropyl C6 compounds are studied as diene precursors in the Diels-Alder reaction. Their rearrangement under different thermal and microwave conditions leads to specific isomeric hexa-, penta- or butadienes, condensed with maleic anhydride as a dienophile. Adduct stereochemistries were compared to those of previously-synthesized model compounds, and are fully characterized with 2D NMR and GC-MS spectroscopies. Some unsaturated terpenes bearing vinylcyclopropane moieties were also condensed, and their adduct structures assigned.
Palabras llave : Microwave; Thermal Diels-Alder Reactions; Diene Precursors; Vinylcyclopropane as a Diene.