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Related Concept Videos

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview01:32

Aldehydes and Ketones with HCN: Cyanohydrin Formation Overview

Cyanohydrins are compounds that contain –CN and –OH groups on the same carbon atom. They are formed by the nucleophilic addition of the cyanide ions to the carbonyl group. Cyanide ions are highly basic and nucleophilic and can be generated from HCN under aqueous conditions. However, since HCN is a weak acid, the number of cyanide ions generated is very small. Hence, a small amount of base or KCN/NaCN is added to HCN to increase the concentration of the cyanide ions in the reaction mixture.
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

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

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.
Formation of Halohydrin from Alkenes02:41

Formation of Halohydrin from Alkenes

An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism01:10

Aldehydes and Ketones with HCN: Cyanohydrin Formation Mechanism

Cyanohydrins are formed when cyanide nucleophiles and carbonyl compounds like aldehydes and ketones react. A strong base, the cyanide ion, catalyzes cyanohydrin formation. The ions are generated from HCN under aqueous conditions. Once the cyanide ions are generated, the first step involves the nucleophilic attack of the cyanide ions on the electrophilic carbonyl carbon. This attack shifts the π electrons from the C=O to the oxygen atom forming the alkoxide ion intermediate. The alkoxide anion...
Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions01:20

Diazonium Group Substitution with Halogens and Cyanide: Sandmeyer and Schiemann Reactions

Arenediazonium substitution reactions occur when the diazonium group is substituted by various functional groups such as halides, hydroxyl, nitrile, etc. For instance, arenediazonium salts react with copper(I) salts of chloride, bromide, or cyanide to form corresponding aryl chlorides, bromides, and nitriles. These reactions are named Sandmeyer reactions. Although the mechanism of this reaction is complicated, as illustrated in Figure 1, they are believed to progress via an aryl copper...
Preparation of Epoxides03:00

Preparation of Epoxides

Overview
Epoxides result from alkene oxidation, which can be achieved by a) air, b) peroxy acids, c) hypochlorous acids, and d) halohydrin cyclization.
Epoxidation with Peroxy Acids
Epoxidation of alkenes via oxidation with peroxy acids involves the conversion of a carbon–carbon double bond to an epoxide using the oxidizing agent meta-chloroperoxybenzoic acid, commonly known as MCPBA. Since the O–O bond of peroxy acids is very weak, the addition of electrophilic oxygen of peroxy acids to...

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Continuous Flow Chemistry: Reaction of Diphenyldiazomethane with p-Nitrobenzoic Acid
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Published on: November 15, 2017

Dynamic combinatorial chemistry with hydrazones: cholate-based building blocks and libraries.

Mark G Simpson1, Michael Pittelkow, Stephen P Watson

  • 1University Chemical Laboratory, University of Cambridge, Lensfield Road, Cambridge, CB2 1EW, United Kingdom.

Organic & Biomolecular Chemistry
|February 19, 2010
PubMed
Summary
This summary is machine-generated.

Researchers developed a new method to create steroidal hydrazides from cholic acid for dynamic combinatorial chemistry. These compounds form macrocyclic N-acyl hydrazone oligomers, showing self-sorting and proof-reading properties.

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Area of Science:

  • Organic Chemistry
  • Supramolecular Chemistry
  • Chemical Biology

Background:

  • Steroidal scaffolds offer unique structural properties for chemical synthesis.
  • Dynamic combinatorial chemistry (DCC) enables the rapid exploration of chemical space.
  • Hydrazone linkages are versatile for constructing dynamic molecular systems.

Purpose of the Study:

  • To develop a general strategy for synthesizing functionalized steroidal hydrazides.
  • To utilize these building blocks in DCC for creating macrocyclic libraries.
  • To investigate the properties and behavior of these dynamic libraries.

Main Methods:

  • Synthesis of dimethyl acetal protected steroidal hydrazides from cholic acid.
  • Deprotection using trifluoroacetic acid (TFA) to initiate library formation.
  • Isolation and characterization of macrocyclic N-acyl hydrazone oligomers using Nuclear Magnetic Resonance (NMR) spectroscopy.

Main Results:

  • Efficient synthesis of steroidal hydrazide building blocks.
  • Formation of diverse macrocyclic N-acyl hydrazone oligomer libraries.
  • Demonstration of tunable equilibrium distribution by modifying substituents and configurations.
  • Observation of exchange properties, proof-reading, and self-sorting in the macrocycles.

Conclusions:

  • The developed strategy provides a robust platform for steroidal DCC.
  • The synthesized macrocycles exhibit controllable self-assembly and information processing capabilities.
  • This work expands the toolkit for designing sophisticated dynamic molecular systems.