Stereoselectivity in the Diels-Alder Cycloadditions of a Facially Dissymmetric Bicyclo[2.2.2]octadiene-Grafted Maleic Anhydride with Exocyclic Butadienes. Unexpected Facial Selectivity in the Cycloaddition with 2,3,5,6-tetramethylidenebicyclo[2.2.2]octene

2003 ◽  
Vol 50 (2) ◽  
pp. 303-312 ◽  
Author(s):  
Teh-Chang Chou ◽  
Liang-Hsuan Kuo ◽  
Kun-Fa Liu
Keyword(s):  
Maleic Anhydride ◽  
Diels Alder ◽  
Facial Selectivity

An AM1 calculational study of the Diels–Alder addition of maleic anhydride to C5-substituted pentamethylcyclopentadienes and 2,5-dimethylthiophene oxide. An attempt to ascertain the factors controlling the π-facial selectivities and relative reactivities

1994 ◽  
Vol 72 (12) ◽  
pp. 2493-2505 ◽  
Author(s):  
Nick Henry Werstiuk ◽  
Jiangong Ma
Keyword(s):  
Maleic Anhydride ◽  
Transition State ◽  
Empirical Method ◽  
Diels Alder ◽  
Facial Selectivity ◽  
Semi Empirical

The Diels–Alder reactions of maleic anhydride (1) with a group of C5-substituted cyclopentadienes and 2,5-dimethylthiophene oxide (5) have been studied with the semi-empirical method AM1. We find that the facial selectivities and relative reactivities found experimentally for six dienes (2a–2f) are accurately reproduced at this level of theory. The results of the calculational study provide no concrete support for the proposal that σ–σ* hyperconjugation in the transition state – an interaction between a σ bond at C5 of the cyclopentadiene and the incipient σ bonds anti to it (the Cieplak effect) – is the major source of the syn facial selectivity observed for 2a–2d. In addition, the relative reactivities and facial selectivities are predicted for a number of cyclopentadienes which will be synthesized and studied experimentally.

ChemInform Abstract: π-Facial Selectivity in Diels-Alder Reactions of C-2-Vinyl Glycals. Stereocontrolled Route to Annulated C-Glycopyranosides.

ChemInform ◽  
1990 ◽  
Vol 21 (48) ◽  
Author(s):  
C. BURNOUF ◽  
J. C. LOPEZ ◽  
F. G. CALVO-FLORES ◽  
M. LOS ANGELES LABORDE ◽  
A. OLESKER ◽  
...  
Keyword(s):  
Diels Alder ◽  
Facial Selectivity

Hetero-Diels-Alder Reactions of Enaminothione with Electrophilic Olefins. Synthesis of 2-Furyl Substituted 2H-Thiopyrans

2002 ◽  
Vol 57 (6) ◽  
pp. 637-644 ◽  
Author(s):  
Krystyna Bogdanowicz-Szwed ◽  
Artur Budzowski
Keyword(s):  
Acetic Acid ◽  
Maleic Anhydride ◽  
Acetic Anhydride ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diethyl Maleate ◽  
Diels Alder Reaction

AbstractThe hetero-Diels-Alder reaction of 1-(2-furyl)-3-(dimethylamino)-2-propene-1-thione (diene) with maleic and fumaric acids, and β-nitrostyrenes yielded 3,4-dihydro-2H-thiopyran derivatives. Treatment of some of those cycloadducts with acetic acid caused elimination of dimethylamine yielding stable 2H-thiopyrans. Reaction of the diene with maleic anhydride furnished a cycloadduct which underwent spontaneous rearrangement to form an N,N-dimethylamide derivative. Cycloadditions of the diene to maleimide, N-phenylmaleimide, diethyl maleate, fumarate and butenolide, carried out in the presence of acetic anhydride,were followed by elimination of dimethylamine, afforded stable 2H-thiopyran derivatives.

Reply to Comment on “Kinetics of a Diels−Alder Reaction of Maleic Anhydride and Isoprene in Supercritical CO2”

2003 ◽  
Vol 107 (43) ◽  
pp. 9249-9249 ◽  
Author(s):  
Evgeni M. Glebov ◽  
Larisa G. Krishtopa ◽  
Victor Stepanov ◽  
Lev N. Krasnoperov
Keyword(s):  
Maleic Anhydride ◽  
Supercritical Co2 ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction ◽  
Kinetics Of
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