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Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

Aldehydes and Ketones with Amines: Imine and Enamine Formation Overview

Primary amines react with carbonyl compounds—aldehydes and ketones—to generate imines. Imines consist of a C=N double bond and are named Schiff bases after its discoverer—the German chemist Hugo Schiff. On the other hand, secondary amines react with carbonyl compounds to give enamines. In enamines, the presence of a C=C double bond adjacent to the nitrogen atom leads to the delocalization of the lone pair.

Acid Halides to Amides: Aminolysis

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 Amines: Reductive Amination of Aldehydes and Ketones

Preparation of Amines: Reductive Amination of Aldehydes and Ketones

Carbonyl compounds and primary amines undergo reductive amination first to produce imines, followed by secondary amines in the same reaction mixture, using selective reducing agents like sodium cyanoborohydride or sodium triacetoxyborohydride. Reductive amination produces different degrees of substitution of amines depending on the starting amine substrate.

Amines to Amides: Acylation of Amines

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...

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Aldehydes and Ketones with Amines: Imine Formation Mechanism

Imine formation involves the addition of carbonyl compounds to a primary amine. It begins with the generation of carbinolamine through a series of steps involving an initial nucleophilic attack and then several proton transfer reactions. The second part includes the elimination of water, as a leaving group, to give the imine.
Imines are formed under mildly acidic conditions. A pH of 4.5 is ideal for the reaction.
If the pH is low or the solution is too acidic, the reaction slows down in the...

Preparation of 1° Amines: Gabriel Synthesis

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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One-step multiple addition of amine to

Isobe¹, Tomita, Nakamura

¹Department of Chemistry, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

Organic Letters

|November 14, 2000

Summary

Researchers developed a new method for synthesizing tetra(amino)fullerene epoxide 1. This one-step process utilizes photochemical aerobic conditions for efficient fullerene functionalization.

Area of Science:

Organic Chemistry
Photochemistry
Materials Science

Background:

Fullerenes, particularly [60]fullerene, are unique carbon allotropes with diverse applications.
Functionalization of fullerenes is crucial for tailoring their properties and expanding their utility.
Developing efficient and selective synthetic routes for fullerene derivatives remains an active area of research.

Purpose of the Study:

To report a novel one-step synthetic method for tetra(amino)fullerene epoxide 1.
To investigate the photochemical aerobic addition of secondary amines to [60]fullerene.
To achieve moderate to excellent yields of the target fullerene derivative.

Main Methods:

Photochemical reaction of [60]fullerene with secondary amines.

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Aerobic conditions were employed during the reaction.

A one-step multiple addition strategy was utilized.

Main Results:

Successful synthesis of tetra(amino)fullerene epoxide 1.
The reaction proceeded via a one-step multiple addition mechanism.
Yields ranged from moderate to excellent, demonstrating the efficiency of the method.

Conclusions:

A novel and efficient one-step synthesis for tetra(amino)fullerene epoxide 1 has been established.
Photochemical aerobic conditions provide a viable route for fullerene functionalization with secondary amines.
The developed method offers a promising approach for accessing complex fullerene derivatives.