The Tiffeneau–Demjanov rearrangement (TDR) is the chemical reaction of a 1-aminomethyl-cycloalkanol with nitrous acid to form an enlarged cycloketone. The Tiffeneau–Demjanov ring expansion, Tiffeneau–Demjanov rearrangement, or TDR, provides an easy way to increase amino-substituted cycloalkanes and cycloalkanols in size by one carbon. Ring sizes from cyclopropane through cyclooctane are able to undergo Tiffeneau–Demjanov ring expansion with some degree of success. Yields decrease as initial ring size increases, and the ideal use of TDR is for synthesis of five, six, and seven membered rings. A principal synthetic application of Tiffeneau–Demjanov ring expansion is to bicyclic or polycyclic systems. Several reviews on this reaction have been published.
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| - Tiffeneau-Ringerweiterung (de)
- Tiffeneau–Demjanov rearrangement (en)
- 蒂芬欧–捷姆扬诺夫重排反应 (zh)
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| - Die Tiffeneau-Ringerweiterung (auch Tiffeneau-Demjanow-Reaktion, -Umlagerung oder -Ringerweiterung) ist eine Namensreaktion aus dem Bereich der Organischen Chemie und beschreibt die Synthese von ringerweiterten, cyclischen Ketonen ausgehend von 1-Aminomethylcycloalkoholen (β-Aminoalkohol). (de)
- The Tiffeneau–Demjanov rearrangement (TDR) is the chemical reaction of a 1-aminomethyl-cycloalkanol with nitrous acid to form an enlarged cycloketone. The Tiffeneau–Demjanov ring expansion, Tiffeneau–Demjanov rearrangement, or TDR, provides an easy way to increase amino-substituted cycloalkanes and cycloalkanols in size by one carbon. Ring sizes from cyclopropane through cyclooctane are able to undergo Tiffeneau–Demjanov ring expansion with some degree of success. Yields decrease as initial ring size increases, and the ideal use of TDR is for synthesis of five, six, and seven membered rings. A principal synthetic application of Tiffeneau–Demjanov ring expansion is to bicyclic or polycyclic systems. Several reviews on this reaction have been published. (en)
- Tiffeneau-Demjanov重排反应(Tiffeneau-Demjanov rearrangement,缩写TDR) 1-氨甲基环烷醇与亚硝酸反应,得到环上多一个碳的环酮。 此反应适用于制 C5~C9 环,尤其是 C5~C7 的环酮。反应底物可由相应的环酮与氰化氢加成后再还原得到,因此该反应是从低级环酮合成多一个碳的高级环酮的一种方法。 反应综述: (zh)
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| - Tiffeneau–Demjanov rearrangement (en)
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| - Rearrangement reaction (en)
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| - Die Tiffeneau-Ringerweiterung (auch Tiffeneau-Demjanow-Reaktion, -Umlagerung oder -Ringerweiterung) ist eine Namensreaktion aus dem Bereich der Organischen Chemie und beschreibt die Synthese von ringerweiterten, cyclischen Ketonen ausgehend von 1-Aminomethylcycloalkoholen (β-Aminoalkohol). (de)
- The Tiffeneau–Demjanov rearrangement (TDR) is the chemical reaction of a 1-aminomethyl-cycloalkanol with nitrous acid to form an enlarged cycloketone. The Tiffeneau–Demjanov ring expansion, Tiffeneau–Demjanov rearrangement, or TDR, provides an easy way to increase amino-substituted cycloalkanes and cycloalkanols in size by one carbon. Ring sizes from cyclopropane through cyclooctane are able to undergo Tiffeneau–Demjanov ring expansion with some degree of success. Yields decrease as initial ring size increases, and the ideal use of TDR is for synthesis of five, six, and seven membered rings. A principal synthetic application of Tiffeneau–Demjanov ring expansion is to bicyclic or polycyclic systems. Several reviews on this reaction have been published. (en)
- Tiffeneau-Demjanov重排反应(Tiffeneau-Demjanov rearrangement,缩写TDR) 1-氨甲基环烷醇与亚硝酸反应,得到环上多一个碳的环酮。 此反应适用于制 C5~C9 环,尤其是 C5~C7 的环酮。反应底物可由相应的环酮与氰化氢加成后再还原得到,因此该反应是从低级环酮合成多一个碳的高级环酮的一种方法。 反应综述: (zh)
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