モルフォリノンの有機触媒環開きポリメリゼーション:機能化されたポリエステルの新しい戦略
Timothy R Blake1, Robert M Waymouth
1Department of Chemistry, Stanford University , Stanford, California 94306, United States.
Journal of the American Chemical Society
|June 20, 2014
まとめ
研究者は,N-置換モルフォリン-2-オンを合成するための新しい方法を開発し,オルガノ触媒環開きポリメリゼーションを通じて機能化されたポリアミノエステルの生成を可能にしました. ポリメリゼーションの成功は,窒素原子のハイブリッド化に依存し,脱保護後,カチオンのポリマーを生成します.
科学分野:
- 有機化学 オーガニック・ケミストリー
- ポリマー化学のポリマー化学について
- カタリシス カタリシス カタリシス
背景:
- N置換のモルフォリン-2-オンは,ポリマー合成における潜在的な応用を持つヘテロサイクリックラクトンです.
- ラクトンのリング開きポリメリゼーション (ROP) は,ポリエステル製造の重要な方法である.
- ROP熱力学に影響を与える要因を理解することは,新しいポリマーの設計に不可欠です.
研究 の 目的:
- N置換モルフォリン-2-オンへの合成経路を開発する.
- これらのモルフォリン-2-オンの有機触媒環開きポリメリゼーションを調査する.
- モルフォリン-2-オンの構造と,そのポリメリゼーション行動の関係を探求する.
主な方法:
- パラジウム触媒を用いたN置換ダイエタノアミンの酸化性ラクトニゼーション.
- N-アシルモルフォリン-2-オンの有機触媒環開きポリメリゼーション.
- ポリメリゼーションの熱力学と窒素原子のピラミデリゼーションを分析するための実験的および理論的研究.
主要な成果:
- N-置換されたモルフォリン-2-オンは,パラジウム触媒による酸化性乳酸化によって合成されました.
- N-アシルモルフォリン-2-オンは,リング開きポリメリゼーションを容易に行い,ポリアミノエステルを形成する.
- ポリメリゼーションは窒素原子のハイブリッド化に敏感であり,N-アリルまたはN-アルキル誘導体はポリメリゼーションを示さない.
- ポリ (N-Boc-morpholin-2-one) の脱保護により,水溶性,カチオン性ポリモルフォリノンが得られます.
結論:
- この研究は,N-置換されたモルフォリン-2-オンと,その後のポリメリゼーションの新種の合成を提示しています.
- 環開きポリメリゼーションの熱力学を制御する重要な要因は,内循環性窒素原子のハイブリッド化である.
- この研究は,機能化されたポリアミノエステルおよびカチオン性ポリマーを作成するための道を開きます.
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