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
Synthetic studies on the avermectins: substituent effects on intramolecular Diels-Alder reactions of N-furfurylacrylamides and further reactions of the cycloadducts
β Scribed by Jung, Michael E.; Street, Leslie J.
- Book ID
- 118037344
- Publisher
- American Chemical Society
- Year
- 1984
- Tongue
- English
- Weight
- 294 KB
- Volume
- 106
- Category
- Article
- ISSN
- 0002-7863
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π SIMILAR VOLUMES
## Abstract Seven alkyl and aryl substituted __N__βallylβ__N__β(methylfuran)βsulfonamide compounds have been synthesized and their rates of cyclization and equilibrium product concentrations determined. Increased steric bulk on the sulfonamide substituent has been shown to increase both the rate of
Comparison of the rates of cyclization of a series of 2-furfuryl methyl fumarates leads to the conclusion that the gem-dimethyl effect is due primarily to higher population of reactive rotamers. Our recent observation of significant rate acceleration of the infmmolecular Diels-Alder reaction of N-f