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Stereochemical control in the intramolecular Diels-Alder reaction with furan

โœ Scribed by Sternbach, Daniel D.; Rossana, Debby M.; Onan, Kay D.

Book ID
127383146
Publisher
American Chemical Society
Year
1984
Tongue
English
Weight
265 KB
Volume
49
Category
Article
ISSN
0022-3263

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๐Ÿ“œ SIMILAR VOLUMES

Stereochemical studies on the intramolec
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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

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Remote substituents that influence ground state state rotamer populations were found to be important controlling factors in the intramolecular Diels-Alder reaction with furan.

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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.