Modeling chemical reactivity. 5. Facial selectivity in Diels-Alder cycloadditions

1987 ◽  
Vol 109 (3) ◽  
pp. 663-666 ◽  
Author(s):  
S. D. Kahn ◽  
W. J. Hehre
Keyword(s):  
Chemical Reactivity ◽  
Diels Alder ◽  
Facial Selectivity

scholarly journals Analysis of the possibility and molecular mechanism of carbon dioxide consumption in the Diels-Alder processes

2021 ◽  
Vol 0 (0) ◽  
Author(s):  
Karolina Kula ◽  
Agnieszka Kącka-Zych ◽  
Agnieszka Łapczuk-Krygier ◽  
Radomir Jasiński
Keyword(s):  
Carbon Dioxide ◽  
Molecular Mechanism ◽  
Lewis Acids ◽  
Chemical Reactivity ◽  
Carbon Dioxide Concentration ◽  
Diels Alder ◽  
Wide Range ◽  
Bet Analysis ◽  
Earth’S Climate ◽  
Step Mechanism

Abstract The large and significant increase in carbon dioxide concentration in the Earth’s atmosphere is a serious problem for humanity. The amount of CO2 is increasing steadily which causes a harmful greenhouse effect that damages the Earth’s climate. Therefore, one of the current trends in modern chemistry and chemical technology are issues related to its utilization. This work includes the analysis of the possibility of chemical consumption of CO2 in Diels-Alder processes under non-catalytic and catalytic conditions after prior activation of the C=O bond. In addition to the obvious benefits associated with CO2 utilization, such processes open up the possibility of universal synthesis of a wide range of internal carboxylates. These studies have been performed in the framework of Molecular Electron Density Theory as a modern view of the chemical reactivity. It has been found, that explored DA reactions catalyzed by Lewis acids with the boron core, proceeds via unique stepwise mechanism with the zwitterionic intermediate. Bonding Evolution Theory (BET) analysis of the molecular mechanism associated with the DA reaction between cyclopentadiene and carbon dioxide indicates that it takes place thorough a two-stage one-step mechanism, which is initialized by formation of C–C single bond. In turn, the DA reaction between cyclopentadiene and carbon dioxide catalysed by BH3 extends in the environment of DCM, indicates that it takes place through a two-step mechanism. First path of catalysed DA reaction is characterized by 10 different phases, while the second by eight topologically different phases.

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

ChemInform Abstract: [(Indenyl)Ru(biphop-F)]+: A Lewis Acid Catalyst that Controls Both the Diene and the Dienophile Facial Selectivity in Diels-Alder Reactions.

ChemInform ◽  
2010 ◽  
Vol 33 (18) ◽  
pp. no-no
Author(s):  
E. Peter Kuendig ◽  
Christophe M. Saudan ◽  
Valerie Alezra ◽  
Florian Viton ◽  
Gerald Bernardinelli
Keyword(s):  
Lewis Acid ◽  
Acid Catalyst ◽  
Diels Alder ◽  
Facial Selectivity ◽  
Lewis Acid Catalyst

Influence of the Sulfinyl Group on the Chemoselectivity and π-Facial Selectivity of Diels−Alder Reactions of(S)-2-(p-Tolylsulfinyl)-1,4-benzoquinone

1996 ◽  
Vol 61 (2) ◽  
pp. 503-509 ◽  
Author(s):  
M. Carmen Carreño ◽  
José L. García Ruano ◽  
Miguel A. Toledo ◽  
Antonio Urbano ◽  
Cynthia Z. Remor ◽  
...  
Keyword(s):  
Diels Alder ◽  
Facial Selectivity ◽  
Sulfinyl Group
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