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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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Introduction
Alkylation of terminal alkynes with primary alkyl halides in the presence of a strong base like sodium amide is one of the common methods for the synthesis of longer carbon-chain alkynes. For example, treatment of 1-propyne with sodium amide followed by reaction with ethyl bromide yields 2-pentyne.
9.9K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.1K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis01:14

Alkylation of β-Diester Enolates: Malonic Ester Synthesis

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Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.
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Preparation of Alkynes: Dehydrohalogenation02:34

Preparation of Alkynes: Dehydrohalogenation

15.6K
Introduction
Alkynes can be prepared by dehydrohalogenation of vicinal or geminal dihalides in the presence of a strong base like sodium amide in liquid ammonia. The reaction proceeds with the loss of two equivalents of hydrogen halide (HX) via two successive E2 elimination reactions.
15.6K
Diels–Alder Reaction Forming Cyclic Products: Stereochemistry01:28

Diels–Alder Reaction Forming Cyclic Products: Stereochemistry

3.8K
The Diels–Alder reaction is one of the robust methods for synthesizing unsaturated six-membered rings. The reaction involves a concerted cyclic movement of six π electrons: four π electrons from the diene and two π electrons from the dienophile.
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Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

3.3K
Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.
3.3K

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Related Experiment Video

Updated: Jun 8, 2025

Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes

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Revisiting the Baddeley Reaction: Access to Functionalized Decalins by Charge-Promoted Alkane Functionalization.

Miloš Vavrík1, Phillip S Grant1, Daniel Kaiser1

  • 1Institute of Organic Chemistry, University of Vienna, Währinger Straße 38, 1090, Vienna, Austria.

Angewandte Chemie (International Ed. in English)
|November 8, 2024
PubMed
Summary

Researchers developed a new method for C-H functionalization of alkanes, enabling regioselective difunctionalization. This breakthrough provides a versatile route to synthesize valuable keto alcohols from simple building blocks.

Keywords:
Baddeley reactionacylium ionalkane functionalizationdecalinoctalin

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Area of Science:

  • Organic Chemistry
  • Catalysis
  • Synthetic Methodology

Background:

  • C-H functionalization of aliphatic compounds lacks regiocontrol due to the absence of directing groups.
  • Difunctionalization reactions face additional challenges in controlling relative stereochemistry.
  • Existing methods like the Baddeley reaction for decalins have limited yield and generality.

Purpose of the Study:

  • To develop a novel, regio- and diastereoselective method for the double functionalization of decalins.
  • To enable access to previously unreported regioisomers in synthetically useful yields.
  • To extend the methodology to other alkane substrates for synthesizing keto alcohols.

Main Methods:

  • Development of a new catalytic system for C-H activation.
  • Application of the method to decalin derivatives for double functionalization.
  • Testing the substrate scope on various simple alkane building blocks.

Main Results:

  • Achieved regio- and diastereoselective double functionalization of decalins.
  • Synthesized a novel, unreported regioisomer in good yields.
  • Demonstrated the method's utility for synthesizing keto alcohols from diverse alkanes.

Conclusions:

  • The developed method overcomes limitations of previous aliphatic C-H functionalization techniques.
  • Provides a powerful and versatile tool for accessing complex molecules from simple alkanes.
  • Opens new avenues for stereocontrolled synthesis in organic chemistry.