The 1,3-dipolar cycloaddition is a chemical reaction between a 1,3-dipole and a dipolarophile to form a five-membered ring. The earliest 1,3-dipolar cycloadditions were described in the late 19th century to the early 20th century, following the discovery of 1,3-dipoles. Mechanistic investigation and synthetic application were established in the 1960s, primarily through the work of Rolf Huisgen.[1] Hence, the reaction is sometimes referred to as the Huisgen cycloaddition (this term is often used to specifically describe the 1,3-dipolar cycloaddition between an organic azide and an alkyne to generate 1,2,3-triazole). 1,3-dipolar cycloaddition is an important route to the regio- and stereoselective synthesis of five-membered heterocycles and their ring-opened acyclic derivatives. The dipolarophile is typically an alkene or alkyne, but can be other pi systems. When the dipolarophile is an alkyne, aromatic rings are generally produced.
1,3- dipolar cycloaddition reaction| course work presentation| by Gobind
1. Submitted by Gobind Kumar
1,3dipolar
cycloaddtion
reactions
IK Gujral Punjab Technical University
PHD COURSE WORK
PRESENTATION
2. • Introduction
• Problem
• Literary Review
• Theoretical Framework
• Objectives
• Hypothesis
• Methodology
• Implementation
• Results
• Analysis
• Conclusion
• Recommendations
• References
MAJOR SECTIONS OF THIS
THESIS DEFENSE PRESENTATION
Overview
3. 1,3 dipolar Cycloadditions
* [(2π + 2e) + 2π] 1,3-dipolar cycloaddition is a reaction where two
organic compounds, a dipolarophile, and a 1,3-dipole (or ylide),
combine to form a five membered heterocycle.
4. 1,3 dipolar Cycloadditions
*This reaction is also referred to as the Huisgen cycloaddition. describe the 1,3-
dipolar cycloaddition between an organic azide and an alkyne to generate 1,2,3-
triazole.
* [(2π + 2e) + 2π] 1,3-dipolar cycloaddition is a reaction where two organic
compounds, a dipolarophile, and a 1,3-dipole (or ylide), combine to form a five
membered heterocycle.
5. 1,3 dipolarcycloaddition
Vs
Diels alder reaction
01 02
*in 1,3 dipolar cycloaddition
reaction a five membered ring is
formed as a end product.
*in diels alder reaction a six
membered ring is formed
as a end product.
*4π system = 1,3 dipole.
*2π system (alkene) = dipolarophile.
*4π system =
diene.
*2π system (alkene) = dienophile.
6. 1,3 dipole
*1,3-dipole is a dipolar compound with delocalized electrons and a separation
of charge over three atoms.
8. 1,3 dipole
vs
dienes
01 02
*1,3 dipole act as both
nucleophile as well as
electrohile.
*in FMO approach- act as
both HOMO as well as
LUMO.
*Dienes act as only
nucleophile.
*In FMO approach- act
as HOMO.
9. Dipolarophile
*dipolarphile- Simple alkene.
*Electron deficient alkene- act as excellent dipolarophile as well
as dienophile.
*α,βunsaturated aldehydes, ketones, and esters, allylic alcohols,
allylic halides, vinylic ethers and alkynes are examples of dipolarophiles
that react readily.
10. Classification of 1,3 dipolar
cycloadditon rxn on the basis
of FMO theory
HOMO-controlled
dipole
or
Nucleophilic
dipole
HOMO-LUMO
controlled dipole
or
Ambhiphilic
dipole
LUMO-controlled
dipole
or
Electrophilic
dipole
Type-I Type-II
Type-III
11. Type-I
*1,3 dipole act as
nucleophile (HOMO).
*dipolarophile act as
electrophile (LUMO)
*electron Poor alkene
required for this
interactions.
24. Problem
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01 02
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Problem
123,456,789
26. 1
2
Literary Review
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28. Overview
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Theoretical
Framework
Proponents
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29. Objectives Apply page animations and transitions to your
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The First Objective
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The Second Objective The Third Objective
Collaborate in real-time with your teammates.
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30. Hypothesis
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31. Methodology Apply page animations and transitions to
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Quantitative Method
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Qualitative Method
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Implementation
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33. 2 out 5
WRITE AN EXPLANATION
OF THE STATISTIC.
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WRITE AN EXPLANATION
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Results
95%
34. Item 1 Item 2 Item 3 Item 4 Item 5
25
20
15
10
5
0
Results
Supported by data from Beal
and Harlow Research, January 2025
Visualize complicated and dense information with
graphs and charts. These are visual aids that help
add more context to the topic you are discussing.
35. Item 1 Item 2 Item 3 Item 4 Item 5
40
30
20
10
0
Results
Supported by data from Beal and
Harlow Research, January 2025
Visualize complicated and dense information
with graphs and charts. These are visual aids
that help add more context to the topic you are
discussing.
36. Item 1
20%
Item 2
20%
Item 3
20%
Item 4
20%
Item 5
20%
Results
Supported by data from Beal
and Harlow Research, January 2025
Visualize complicated and dense information with
graphs and charts. These are visual aids that help
add more context to the topic you are discussing.
37. Analysis
The First Analysis of
Obtained Results
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The Third Analysis of
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38. Start inspired with thousands of templates,
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Conclusion
39. Recommendations
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40. References
Natural Science Edition 1 by D.B. Stanley (Book)
01
The Circle of Life by Sari Purdue (Article)
02
Our Great Ancestors by Elliot Sterling (Article)
03
Our World by Beal and Harlow Productions (Video)
04
The Great Evolution by Keel and Briar Group (Research Paper)
05
44. Student Resource Page
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