Reactions of Vinylcyclopropane and Bicyclopropyl Compounds With Maleic Anhydride
Keywords:Microwave, Thermal Diels-Alder Reactions, Diene Precursors, Vinylcyclopropane as a Diene
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.
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32. The above mentioned difficulties are related to the six carbon or lower chains of dienes involved and to the cyclopropylcarbinols.
The other isomeric model C6 dienes were not commercially accessible . Some of them cannot be obtained from the cyclopropane compounds of this study and then are not potential diene precursors.
33. The small volume stainless steel vessel conditions are relatively close to those applied in using the MW methods.
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