Synthetic and kinetic studies of substituent effects in the furan intramolecular Diels-Alder reaction

Tetrahedron ◽  
1994 ◽  
Vol 50 (23) ◽  
pp. 6767-6782 ◽  
Author(s):  
Brian J. McNelis ◽  
Daniel D. Sternbach ◽  
Andrew T. MacPhail
Keyword(s):  
Substituent Effects ◽  
Kinetic Studies ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

scholarly journals Substituent Effects on Regioselectivity of the Diels-Alder Reactions: Reactions of 10-Allyl-1,8-dichloroanthracene with 2-Chloroacrylonitrile, 1-Cyanovinyl Acetate and Phenyl Vinyl Sulfone

2016 ◽  
Vol 2016 ◽  
pp. 1-5 ◽  
Author(s):  
Mujeeb A. Sultan ◽  
Usama Karama
Keyword(s):  
Nmr Spectra ◽  
Steric Effect ◽  
Substituent Effects ◽  
Alder Reaction ◽  
Diels Alder ◽  
Vinyl Sulfone ◽  
Diels Alder Reaction ◽  
Phenyl Vinyl

Diels-Alder reaction of 10-allyl-1,8-dichloroanthracene (3) with 2-chloroacrylonitrile (4) and 1-cyanovinyl acetate (5) gives exclusively theorthoisomer while its reaction with phenyl vinyl sulfone (10) yields a mixture of two isomeric adducts with priority toorthoisomer. The reactions proceeded under microwave condition in xylene. Configurations of these isomers have been assigned with the help of NMR spectra. The results indicated that the steric effect is dominating toward the isomer regioselectivity in the Diels-Alder reaction of the present compounds.

Substituent Effects in the Hetero-Diels−Alder Reaction of Thiocarbonyl Compounds with Butadiene

1996 ◽  
Vol 61 (15) ◽  
pp. 5121-5129 ◽  
Author(s):  
Vincenzo Barone ◽  
Roger Arnaud ◽  
Pierre Yves Chavant ◽  
Yannick Vallée
Keyword(s):  
Substituent Effects ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction
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