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Solid-phase Submonomer Synthesis of Peptoid Polymers and their Self-Assembly into Highly-Ordered Nanosheets
Published on: November 2, 2011
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Alkylating Polymers: Resin-Released Carbenium Ions as Versatile Reactive Intermediates in Polymer-Assisted
Jörg Rademann1, Joachim Smerdka1, Günther Jung1
1Institut für Organische Chemie Universität Tübingen Auf der Morgenstelle 18, 72076 Tübingen (Germany) Fax.: (+49) 7071-295560.
Angewandte Chemie (International Ed. in English)
|May 2, 2018
Summary
New solid-supported alkylating polymers, synthesized as 3-alkyl-1-aryltriazenes, enable efficient esterification of carboxylic acids and complex mixtures via carbenium ion release upon acid activation.
Area of Science:
- Organic Chemistry
- Polymer Chemistry
- Synthetic Methodology
Background:
- Esterification is a fundamental organic transformation.
- Traditional methods can involve harsh conditions or generate waste.
- Development of cleaner, solid-supported reagents is desirable.
Purpose of the Study:
- To develop novel solid-supported reagents for esterification.
- To synthesize and characterize solid-supported diazoalkane analogues.
- To demonstrate their utility in esterifying carboxylic acids and complex mixtures.
Main Methods:
- Synthesis of solid-supported 3-alkyl-1-aryltriazenes.
- Acidic activation of the polymers to generate carbenium ions.
- Reaction of the activated polymers with carboxylic acids.
Main Results:
- The synthesized polymers effectively alkylate carboxylic acids.
- Clean and smooth esterification was achieved.
- The method is applicable to complex compound mixtures.
Conclusions:
- Solid-supported 3-alkyl-1-aryltriazenes are effective reagents for esterification.
- This approach offers a cleaner alternative for synthesizing esters.
- The methodology is suitable for diverse substrates.
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