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Related Concept Videos

Aldehydes and Ketones with Amines: Imine Formation Mechanism01:23

Aldehydes and Ketones with Amines: Imine Formation Mechanism

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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.
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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.
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Aldehydes and Ketones with Amines: Enamine Formation Mechanism01:14

Aldehydes and Ketones with Amines: Enamine Formation Mechanism

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Enamine formation involves the addition of carbonyl compounds to a secondary amine through a series of reactions. The mechanism begins with the generation of carbinolamine, a nucleophilic attack followed by several proton transfer reactions. The hydroxyl group of the carbinolamine is converted into water to make a better leaving group that can push the reaction forward by eliminating a water molecule. In enamine formation, the last step involves the abstraction of a proton from the α...
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Acid Halides to Amides: Aminolysis01:07

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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.
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Amines to Alkenes: Hofmann Elimination01:16

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Alkenes can be obtained from amines via an E2 elimination. The amine is first converted into a good leaving group, such as a quaternary ammonium salt. This is accomplished by treating the amine with an excess of alkyl halide, which results in a halide salt. Next, the halide salt is transformed into a hydroxide salt that functions as a base to enable elimination.
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Preparation of Amines: Reductive Amination of Aldehydes and Ketones01:38

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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.
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A General Method for Imine Formation Using B(OCH2CF3)3.

Jonathan T Reeves1, Michael D Visco1, Maurice A Marsini1

  • 1Chemical Development, Boehringer Ingelheim Pharmaceuticals, Inc., 900 Ridgebury Road/P.O. Box 368, Ridgefield, Connecticut 06877-0368, United States.

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Summary
This summary is machine-generated.

Tris(2,2,2-trifluoroethyl)borate is a mild reagent for synthesizing diverse imines from amides/amines and carbonyl compounds. This efficient method works at room temperature, simplifying imine formation and product isolation.

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Area of Science:

  • Organic Chemistry
  • Synthetic Chemistry

Background:

  • Imines are crucial intermediates in organic synthesis.
  • Developing mild and efficient methods for imine synthesis is an ongoing challenge.

Purpose of the Study:

  • To investigate the utility of Tris(2,2,2-trifluoroethyl)borate as a reagent for imine formation.
  • To establish a mild and general method for synthesizing various aldimines.

Main Methods:

  • Condensation reactions between amides or amines and carbonyl compounds.
  • Utilizing Tris(2,2,2-trifluoroethyl)borate as the key reagent.
  • Performing reactions at room temperature.

Main Results:

  • Tris(2,2,2-trifluoroethyl)borate effectively promotes the formation of a wide range of imines.
  • Various N-substituted aldimines, including N-Sulfinyl, N-toluenesulfonyl, and N-diphenylphosphinoyl derivatives, were successfully synthesized.
  • The reactions proceeded smoothly at room temperature, yielding products without complex workup procedures.

Conclusions:

  • Tris(2,2,2-trifluoroethyl)borate is a versatile and mild reagent for general imine synthesis.
  • This method offers operational simplicity and efficiency for accessing diverse aldimines.