A variety of substituted furans a-6J undergo the intramolecular Die&Alder reaction at high pressure (12.5 kbar) to provide oxatricyclo adducts Q-12) within 24 hours at room temperature.
Intramolecular Diels-Alder reactions of the furan diene
β Scribed by Kathlyn A. Parker; Mark R. Adamchuk
- Publisher
- Elsevier Science
- Year
- 1978
- Tongue
- French
- Weight
- 211 KB
- Volume
- 19
- Category
- Article
- ISSN
- 0040-4039
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An internal Diels-Alder reaction, using furan as the diene component, formed a highly functionalized 5-membered carbocycllc ring in excellent yield. Solvent and substituent effects of this reaction were examined. In connection with a proJect devoted to the synthesis of some natural products contai
2-(2'-Furfuryl)-N-aczyloyl tetrahydm-1 ~-henzoxaz~ 2a participates in diastercoselective intramolecular Diels-Alder reaction in very mild conditions leading to two diasterecisemeric exo-adduets with good diastereoseleclivity. Chromatographic sel~ration of both adduts, and further elimination of the