Stereospecific Synthesis of Fluorinated Pyrazolidinones and Isoxazolidines via a Catalyst-Free 1,3-Dipolar Cycloaddition of β-Fluoroalkylated α,β-Unsaturated 2-Pyridylsulfones

2018 ◽  
Vol 7 (9) ◽  
pp. 1830-1834 ◽  
Author(s):  
Ying-Da Kou ◽  
Zhen-Ni Zhao ◽  
Xing Yang ◽  
Subarna Jyoti Kalita ◽  
Xue-Jian Chen ◽  
...  
Keyword(s):  
Stereospecific Synthesis ◽  
Dipolar Cycloaddition ◽  
Catalyst Free

Catalyst-Free Synthesis of N-(1,7-Dioxotetrahydropyrazolo[1,2-a]pyrazol-2-yl)benzamide Derivatives by 1,3-Dipolar Cycloaddition and Rearrangement

Synlett ◽  
2014 ◽  
Vol 25 (08) ◽  
pp. 1093-1096 ◽  
Author(s):  
Yu Xu ◽  
Wenjing Liu ◽  
Xingxia Sun ◽  
Dapeng Lu ◽  
Lijuan Guo
Keyword(s):  
Dipolar Cycloaddition ◽  
Catalyst Free ◽  
Benzamide Derivatives

Catalyst-free 1,3-dipolar cycloaddition of 3-nitrochromen with sodium azide: a facile method for the synthesis of 4-aryl-1,4-dihydrochromeno[4,3-d][1,2,3]triazole derivatives

Tetrahedron ◽  
2009 ◽  
Vol 65 (29-30) ◽  
pp. 5799-5804 ◽  
Author(s):  
Pateliya Mujjamil Habib ◽  
B. Rama Raju ◽  
Veerababurao Kavala ◽  
Chun-Wei Kuo ◽  
Ching-Fa Yao
Keyword(s):  
Sodium Azide ◽  
Dipolar Cycloaddition ◽  
Triazole Derivatives ◽  
Catalyst Free

Beyond the Alternatives that Switch the Mechanism of the 1,3-Dipolar CyCloadditions from Concerted to Stepwise or Vice Versa: A Literature Review

2016 ◽  
Vol 41 (4) ◽  
pp. 331-344 ◽  
Author(s):  
Seyyed Amir Siadati
Keyword(s):  
Organic Chemistry ◽  
Literature Review ◽  
Cycloaddition Reaction ◽  
Dipolar Cycloaddition ◽  
Stepwise Mechanism ◽  
Dipolar Cycloadditions ◽  
Catalyst Free ◽  
Number Of Factors ◽  
Reaction Channels ◽  
The 1960S

For several decades, the concerted or stepwise character of the mechanism of the 1,3-dipolar cycloaddition reaction has been one of the most debated issues in the field of organic chemistry. The significance of this problem is due to the fact that in a catalyst-free 1,3-dipolar cycloaddition, when the mechanism switches from concerted to stepwise, the stereospecificity is lost and thus unwanted stereoisomers may emerge. The first proposals about the mechanism of the 1,3-dipolar reaction were due to Huisgen (concerted model) and subsequently by Firestone (two-step diradical channel) in the 1960s. After a decade of debate, most researchers accepted the concerted model for the reaction, but during these years, researchers reported some examples of the stepwise mechanism for catalyst-free 1,3-dipolar cycloadditions. This review attempts to find a number of factors that could influence the reaction channels and switch the mechanism from concerted to stepwise, or vice versa.

Synthesis and Characterization of Reactive Energetic Plasticizers for Poly(glycidyl azide-co-tetramethylene glycol)-Based Polyurethane Binders

2021 ◽  
Vol 21 (7) ◽  
pp. 4110-4115
Author(s):  
Yechen Shen ◽  
Younghwan Kwon
Keyword(s):  
Click Reaction ◽  
Point Of View ◽  
Dipolar Cycloaddition ◽  
Synthesis And Characterization ◽  
Catalyst Free ◽  
Energetic Plasticizers ◽  
Glycidyl Azide

Two reactive energetic plasticizers, 3-((2,2-dinitropropoxy)methoxy)prop-1-yne and 4-((2,2-dinitropropoxy)methoxy)but-1-yne which can react with an azido-containing poly(glycidyl azide-co-tetramethylene glycol) prepolymer by cupper-free 1,3-dipolor cycloaddition (“Click”) reaction, were synthesized and characterized, in order to investigate their plasticizing performance and catalyst-free 1,3-dipolar cycloaddition reactivity on energetic polyurethane binders. Two reactive energetic plasticizers showed better plasticizing performance than commercial energetic plasticizers. In the reactivity point of view, 3-((2,2-dinitropropoxy)methoxy)prop-1-yne exhibited higher Click reactivity than 4-((2,2-dinitropropoxy)methoxy)but-1-yne. Two synthesized plasticizers were found to fulfill the requirements for use as reactive energetic plasticizers.

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