Intramolecular Diels-Alder reactions with furan: The gem-dialkyl effect revisited
β Scribed by Daniel D. Sternbach; Debby M. Rossana; Kay D. Onan
- Publisher
- Elsevier Science
- Year
- 1985
- Tongue
- French
- Weight
- 242 KB
- Volume
- 26
- Category
- Article
- ISSN
- 0040-4039
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β¦ Synopsis
Remote substituents that influence ground state state rotamer populations were found to be important controlling factors in the intramolecular Diels-Alder reaction with furan.
π SIMILAR VOLUMES
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
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.
## 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
The stereochemical outcome of intramolecular Diels-Alder reactions of furans with Z-and E-2-ene-1,4-dione units attached by a bridging chain to C-2 of the furan results from modification of the steric demands of the bridging chain by the preference of the external activating group to adopt an endost
Depending on the reaction conditions the intramolecular Diels-Alder reaction of furan-diene 14 yields predominantly either one of two adducts 16a and 16b , which possess the necessary --functionality for eventual transformation into corticosteroids. The dienophile was intro-