Going beyond the barriers of aza-Michael reactions: controlling the selectivity of acrylates towards primary amino-PDMS
| Autor: | François Ganachaud, Emmanuel Pouget, Sandra Binauld, Daniel Portinha, Aymeric Genest, Etienne Fleury |
|---|---|
| Přispěvatelé: | Ingénierie des Matériaux Polymères (IMP), Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS)-Université Jean Monnet [Saint-Étienne] (UJM)-Institut National des Sciences Appliquées de Lyon (INSA Lyon), Institut National des Sciences Appliquées (INSA)-Université de Lyon-Institut National des Sciences Appliquées (INSA)-Université de Lyon-Université Claude Bernard Lyon 1 (UCBL), Université de Lyon, Institut Charles Gerhardt Montpellier - Institut de Chimie Moléculaire et des Matériaux de Montpellier (ICGM ICMMM), Ecole Nationale Supérieure de Chimie de Montpellier (ENSCM)-Centre National de la Recherche Scientifique (CNRS)-Université de Montpellier (UM)-Université Montpellier 1 (UM1)-Université Montpellier 2 - Sciences et Techniques (UM2)-Institut de Chimie du CNRS (INC), Université de Lyon-Institut National des Sciences Appliquées (INSA)-Université de Lyon-Institut National des Sciences Appliquées (INSA)-Université Claude Bernard Lyon 1 (UCBL) |
| Rok vydání: | 2017 |
| Předmět: |
chemistry.chemical_classification
Primary (chemistry) Polymers and Plastics Double bond 010405 organic chemistry Chemistry Organic Chemistry Bioengineering [CHIM.MATE]Chemical Sciences/Material chemistry 010402 general chemistry 01 natural sciences Biochemistry 0104 chemical sciences Solvent [CHIM.POLY]Chemical Sciences/Polymers Hydrocarbon Polymer chemistry Organic chemistry Amine gas treating Metal catalyst Selectivity ComputingMilieux_MISCELLANEOUS |
| Zdroj: | Polymer Chemistry Polymer Chemistry, Royal Society of Chemistry-RSC, 2017, 8 (3), pp.624-630. ⟨10.1039/c6py01802e⟩ |
| ISSN: | 1759-9962 1759-9954 |
| DOI: | 10.1039/c6py01802e |
| Popis: | The aza-Michael reaction of aliphatic primary amines with electron-deficient double bonds proceeds through two additions possibly leading to a mixture of amines with different degrees of substitution. We present here model reactions involving acrylates as Michael acceptors and amino-PDMS as Michael donors, and the impact of experimental conditions (temperature, organo-catalyst, and solvent) on the selectivity of such a reaction. While hydrocarbon alcohols favor monoaddition, halogenated alcohols favor double substitution. Tuning the operating conditions allowed the formation of either a monoadduct or a diadduct with no primary amine left, demonstrating that the structure of PDMS can be modified in a controlled manner without using any metal catalyst. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|