Electronic Effects on the Stereochemistry of the Diels—Alder Reaction1

1963 ◽  
Vol 28 (6) ◽  
pp. 1593-1596 ◽  
Author(s):  
Fred Kaplan ◽  
Harold Conroy
Keyword(s):  
Diels Alder ◽  
Electronic Effects

Intramolecular Diels-Alder reactions of furan derivatives: Steric and electronic effects of trifluoromethyl groups

1992 ◽  
Vol 57 (1-3) ◽  
pp. 239-243 ◽  
Author(s):  
Makoto Suzuki ◽  
Tomoko Okada ◽  
Takeo Taguchi ◽  
Yuji Hanzawa ◽  
Yoichi Iitaka
Keyword(s):  
Diels Alder ◽  
Electronic Effects ◽  
Furan Derivatives ◽  
Trifluoromethyl Groups

ELECTRONIC EFFECTS AND RATES IN THE DIELS-ALDER REACTION

1952 ◽  
Vol 17 (2) ◽  
pp. 201-206 ◽  
Author(s):  
JOSEPH J. DUDKOWSKI ◽  
ERNEST I. BECKER
Keyword(s):  
Alder Reaction ◽  
Diels Alder ◽  
Electronic Effects ◽  
Diels Alder Reaction

Studies of electronic effects of modified pyridine-imine ligands utilized in cobalt-catalyzed meta-selective Diels–Alder reactions

2014 ◽  
Vol 749 ◽  
pp. 219-223 ◽  
Author(s):  
Gerhard Hilt ◽  
Judith Janikowski ◽  
Martin Schwarzer ◽  
Olaf Burghaus ◽  
Dimitri Sakow ◽  
...  
Keyword(s):  
Diels Alder ◽  
Electronic Effects ◽  
Imine Ligands

DFT study of the stereo-selectivity of oxygenated heterocycles from 10 to 12 links

2013 ◽  
Vol 91 (9) ◽  
pp. 811-820
Author(s):  
Hafida Merouani ◽  
Christophe Morell ◽  
Nadia Ouddai ◽  
Henry Chermette
Keyword(s):  
Experimental Evidence ◽  
Chemical Reactivity ◽  
Diels Alder ◽  
Conceptual Dft ◽  
Dft Study ◽  
Electronic Effects ◽  
Transition Structure ◽  
Dual Descriptor ◽  
Ring Strain ◽  
Stereo Selectivity

Intra-molecular Diels–Alder (IMDA) reactions of tethered trienes can furnish two distinct diastereoisomeric products, the cis (i.e., endo) stereoisomer and the trans (i.e., exo) stereoisomer. Experimental evidence shows a quite high cis stereo-selectivity for 10-link compounds (cis/trans = 70:30), while 11- and 12-links compounds exhibit no particular selectivity. DFT (B3LYP/6-31G*) computations provide useful insights into the origins of this amazing stereo-selectivity. The cyclization path towards trans stereo-isomer is always thermodynamically favored, whatever the size of the system. The high cis stereo-selectivity displayed by the 10-link system is kinetically controlled by a tug-of-war between ring strain and electronic effects in the transition structure. The dual descriptor of chemical reactivity, a conceptual DFT based descriptor designed to delineate electronic effects, has been used to unravel the stabilizing processes that take place at the TSs.

scholarly journals Aromatic heterocycles XII. Semiempirical PM3 study of Diels-Alder cycloaddition reaction of substituted phosphabenzenes

2004 ◽  
Vol 2 (1) ◽  
pp. 34-51
Author(s):  
Liliana Pacureanu ◽  
Mircea Mracec ◽  
Zeno Simon
Keyword(s):  
Steric Hindrance ◽  
Reasonable Agreement ◽  
Cycloaddition Reaction ◽  
Diels Alder ◽  
Electronic Effects ◽  
Reaction Energy ◽  
Aromatic Heterocycles ◽  
Electronic Effects Of Substituents

AbstractWe report the results of a semiempirical PM3 study of the 1,4 cycloaddition reaction of substituted λ3-phosphabenzenes with alkynes. The influence of the nature, position and steric hindrance of substituents on the reaction energy is studied. Except for some values, the results are in reasonable agreement with experimental observations and electronic effects of substituents.

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