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Preparation of Alkynes: Alkylation Reaction02:27

Preparation of Alkynes: Alkylation Reaction

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.
Acid Halides to Amides: Aminolysis01:07

Acid Halides to Amides: Aminolysis

Aminolysis is a nucleophilic acyl substitution reaction, where ammonia or amines act as nucleophiles to give the substitution product. Acid halides react with ammonia, primary amines, and secondary amines to yield primary, secondary, and tertiary amides, respectively.
In the first step of the aminolysis mechanism, the amine attacks the carbonyl carbon of the acyl chloride to form a tetrahedral intermediate. In the second step, the carbonyl group is re-formed with the elimination of a chloride...
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...
Preparation of 1° Amines: Azide Synthesis01:22

Preparation of 1° Amines: Azide Synthesis

Direct alkylation of ammonia produces polyalkylated amines, along with a quaternary ammonium salt. To exclusively prepare primary amines, the azide synthesis method can be used.
Azide ions act as good nucleophiles and react with unhindered alkyl halides to form alkyl azides. Alkyl azides do not participate in further nucleophilic substitution reactions, thereby eliminating the chances of polyalkylated products. Alkyl azides are reduced by hydride-based reducing agents, like lithium aluminum...
Amines to Amides: Acylation of Amines01:19

Amines to Amides: Acylation of Amines

Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
Next, the second equivalent of amine serves as a Brønsted base and deprotonates the quaternary amide...
Preparation of 1° Amines: Gabriel Synthesis01:28

Preparation of 1° Amines: Gabriel Synthesis

Direct alkylation is not a suitable method for synthesizing amines because it produces polyalkylated products. Gabriel synthesis is the most preferred method to exclusively make primary amines. The method uses phthalimide, which contains a protected form of nitrogen that participates in alkylation only once to predominantly give primary amines.
Strong bases like NaOH or KOH deprotonate the phthalimide to form the corresponding anion, which acts as a nucleophile. Further, the anion attacks an...

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives
08:43

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Published on: January 19, 2016

Efficient synthesis of acylsilanes using morpholine amides.

Christopher T Clark1, Benjamin C Milgram, Karl A Scheidt

  • 1Department of Chemistry, Northwestern University, 2145 Sheridan Road, Evanston, Illinois 60208, USA.

Organic Letters
|October 22, 2004
PubMed
Summary

A new, economical method synthesizes acylsilanes using morpholine amides and silyllithium. This approach avoids over-addition and toxic reagents, yielding high-quality acylsilanes efficiently.

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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Facile Preparation of (2Z,4E)-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
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Published on: February 7, 2019

Area of Science:

  • Organic Chemistry
  • Organosilicon Chemistry

Background:

  • Acylsilanes are versatile synthetic intermediates.
  • Traditional synthesis methods often involve toxic reagents like copper(I) cyanide and can suffer from over-addition.
  • Morpholine amides offer a potentially more economical and controlled precursor.

Purpose of the Study:

  • To develop a general, efficient, and economical synthesis of acylsilanes.
  • To explore the use of morpholine amides as precursors for acylsilane synthesis.
  • To circumvent the need for stoichiometric copper(I) cyanide in acylsilane preparation.

Main Methods:

  • Reaction of morpholine amides with silyllithium species.
  • Purification and characterization of the resulting acylsilanes.

Main Results:

  • A general synthetic route to acylsilanes from morpholine amides was established.
  • The use of morpholine amides effectively prevented over-addition of the silyl nucleophile.
  • The procedure yielded acylsilanes in good yields with high purity.
  • This method avoids the use of stoichiometric copper(I) cyanide.

Conclusions:

  • Morpholine amides are effective and economical precursors for acylsilane synthesis.
  • The described method offers a cleaner and more efficient alternative to existing acylsilane syntheses.
  • This new procedure broadens the accessibility of acylsilanes for further chemical transformations.