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Related Concept Videos

Preparation of Amides01:29

Preparation of Amides

Amides are synthesized by treating carboxylic acids with amines in the presence of dehydrating agents like dicyclohexylcarbodiimide (DCC).
The DCC-promoted synthesis of amides begins with the protonation of DCC by carboxylic acid. The protonation makes it a better acceptor. Next, the addition of carboxylate to the protonated carbodiimide gives a reactive acylating agent.
Subsequently, the amine acts as a nucleophile that attacks the acylating agent to form a tetrahedral intermediate. In the...
Carboxylic Acids to Methylesters: Alkylation using Diazomethane01:33

Carboxylic Acids to Methylesters: Alkylation using Diazomethane

Carboxylic acids react with diazomethane in an ether solvent via alkylation at the carboxylate oxygen atom to give methyl esters of the corresponding acid with excellent yields.
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
Nomenclature of Primary Amines01:17

Nomenclature of Primary Amines

Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR

The axial and equatorial protons in cyclohexane can be distinguished by performing a variable-temperature NMR experiment. In this process, except for one proton, the remaining eleven protons are replaced by deuterium. The deuterium substitution avoids the possible peak splitting caused by the spin-spin coupling between the adjacent protons. The remaining proton flips between the axial and equatorial positions.

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Related Experiment Video

Updated: May 19, 2026

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives
09:22

Self-assembling Morphologies Obtained from Helical Polycarbodiimide Copolymers and Their Triazole Derivatives

Published on: February 7, 2017

N,N-dimethylformamide: a multipurpose building block.

Shengtao Ding1, Ning Jiao

  • 1State Key Laboratory of Natural and Biomimetic Drugs, School of Pharmaceutical Sciences, Peking University, Xue Yuan Road 38, Beijing 100191, China.

Angewandte Chemie (International Ed. in English)
|August 30, 2012
PubMed
Summary

N,N-dimethylformamide (DMF) is a versatile reagent in organic synthesis. This review highlights recent advancements in using DMF for formylation, aminocarbonylation, amination, amidation, cyanation, and reactions with arynes.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • N,N-dimethylformamide (DMF) is a widely used solvent and reagent in organic synthesis.
  • Its role as a multipurpose precursor in various chemical reactions is well-established.
  • Numerous reviews cover its applications, but recent developments warrant a focused summary.

Purpose of the Study:

  • To summarize recent advancements in the utilization of N,N-dimethylformamide (DMF) as a precursor in organic synthesis.
  • To focus on the performance of DMF in specific reaction types, including formylation, aminocarbonylation, amination, amidation, and cyanation.
  • To review the reactivity of DMF with arynes.

Main Methods:

  • Literature review of recent developments in organic synthesis involving DMF.
  • Analysis of DMF's performance as a precursor in key synthetic transformations.
  • Compilation of examples illustrating DMF's utility in formylation, aminocarbonylation, amination, amidation, cyanation, and reactions with arynes.

Main Results:

  • DMF serves as a valuable precursor for introducing various functional groups in organic molecules.
  • Recent studies demonstrate enhanced efficiency and scope when using DMF in formylation, aminocarbonylation, amination, amidation, and cyanation reactions.
  • The reactivity of DMF with arynes has been further explored, revealing new synthetic pathways.

Conclusions:

  • N,N-dimethylformamide (DMF) remains a crucial and versatile reagent in modern organic synthesis.
  • Recent developments underscore its continued importance in facilitating key synthetic transformations.
  • Further exploration of DMF's reactivity promises new avenues for chemical synthesis.