Chemical consequences of fluorine substitution. Part 1. Experimental and theoretical results on Diels–Alder reactions of α- and β-fluorostyrenes†

2001 ◽  
pp. 1929-1938 ◽  
Author(s):  
Thomas Ernet ◽  
Andreas H. Maulitz ◽  
Ernst-Ulrich Würthwein ◽  
Günter Haufe
Keyword(s):  
Diels Alder ◽  
Fluorine Substitution ◽  
Theoretical Results

ChemInform Abstract: Theoretical Results on Hetero-Diels-Alder Reactions

ChemInform ◽  
2010 ◽  
Vol 30 (24) ◽  
pp. no-no
Author(s):  
J. Gonzalez ◽  
J. A. Sordo
Keyword(s):  
Diels Alder ◽  
Theoretical Results

AN ANALYSIS OF THE REGIOSELECTIVITY IN HETERO DIELS–ALDER REACTIONS USING DFT-BASED REACTIVITY INDEXES

2006 ◽  
Vol 05 (02) ◽  
pp. 197-206 ◽  
Author(s):  
H. CHEMOURI ◽  
S. M. MEKELLECHE
Keyword(s):  
Diels Alder ◽  
Maximum Hardness ◽  
Activation Barriers ◽  
Reactivity Indexes ◽  
Maximum Hardness Principle ◽  
Theoretical Results

The regioselectivity of hetero Diels–Alder reactions (HDA) of 2-azabutadiene with aldehydes has been elucidated by means of Gazquez–Mendez rules, which are based on the calculation of local softnesses of the four terminal atoms involved in cyclization. The theoretical results obtained with the B3LYP/6-31G(d) method confirm the regioselectivities observed experimentally for all substituents ( R = H , CH 3, CN ) present in the aldehyde reactant. The regioselectivities of these HDA reactions have been confirmed by the calculation of the activation barriers corresponding to the two cyclization modes, and also by the application of the Houk rule and the maximum hardness principle.

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