A theoretical study of the copper(i)-catalyzed 1,3-dipolar cycloaddition reaction in dabco-based ionic liquids: the anion effect on regioselectivity

2010 ◽  
Vol 12 (8) ◽  
pp. 1958 ◽  
Author(s):  
Cinzia Chiappe ◽  
Benedetta Mennucci ◽  
Christian Silvio Pomelli ◽  
Angelo Sanzone ◽  
Alberto Marra
Keyword(s):  
Ionic Liquids ◽  
Theoretical Study ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Anion Effect

Copper nanoparticles in ionic liquids: Recyclable and efficient catalytic system for 1,3-dipolar cycloaddition reaction

2009 ◽  
Vol 10 (8) ◽  
pp. 1240-1243 ◽  
Author(s):  
Dilip Raut ◽  
Karuna Wankhede ◽  
Vipraja Vaidya ◽  
Sachin Bhilare ◽  
Nitin Darwatkar ◽  
...  
Keyword(s):  
Ionic Liquids ◽  
Catalytic System ◽  
Copper Nanoparticles ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition

An experimental and theoretical study on the regioselective synthesis of a new class of spiropyrrolothiazoles with quinoxaline motifs via a 1,3-dipolar cycloaddition reaction. An evaluation of DFT methods

RSC Advances ◽  
2015 ◽  
Vol 5 (93) ◽  
pp. 76368-76376 ◽  
Author(s):  
Mahshid Hamzehloueian ◽  
Yaghoub Sarrafi ◽  
Zahra Aghaei
Keyword(s):  
Theoretical Study ◽  
Cycloaddition Reaction ◽  
Regioselective Synthesis ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Dft Methods ◽  
Π Interactions ◽  
New Class

Evaluation of B3LYP/6-31G(d,p), wB97xD/6-31G(d,p) and M06-2X/6-31G(d,p) methods revealed the importance of π/π interactions in regio- and stereoselectivity of cycloaddition reactions.

A THEORETICAL STUDY ON THE MECHANISM OF 2:1 1, 3 DIPOLAR CYCLOADDITION REACTIONS

2007 ◽  
Vol 06 (04) ◽  
pp. 861-867 ◽  
Author(s):  
JING-FANG WANG ◽  
DONG-QING WEI ◽  
CHUN-FANG WANG ◽  
YONG YE ◽  
YI-XUE LI ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Organic Synthesis ◽  
Density Functional ◽  
Theoretical Study ◽  
Cycloaddition Reaction ◽  
Density Functional Theory Calculations ◽  
Biologically Active ◽  
Dipolar Cycloaddition ◽  
Functional Theory ◽  
Nitrile Oxides

The reactions between nitrile oxides and alkenes are of considerable interest in organic synthesis as the resulting heterocycles are versatile intermediates for the synthesis of natural products and biologically active compounds. In this paper, we design a series of reactions of phosphonyl nitrile oxides with acrylonnitrile, which can give 2:1 cycloaddition products with no crystal structure released so far, and present a detailed theoretical study on the mechanism of the 2:1 1, 3-dipolar cycloaddition reaction, which has been explored with density functional theory calculations at B3LYP/6-31G* level. The results reveal that the following mechanism is quite possible. Firstly, it starts as a normal 1,3-dipolar cycloaddition reaction to produce a regiospecific 1:1 product. Subsequently, highly reactive diisopropanyl phosphonyl nitrile oxide sequentially reacts with the aforementioned regiospecific 1:1 product and gives the corresponding cycloadduct. Further study is underway to expand the scope of this methodology, as well as to ascertain mechanistic details of the cycloaddition process.

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