齊齊巴賓吡啶合成

齊齊巴賓吡啶合成（英語：Chichibabin pyridine synthesis）^[1]^[2]^[3]是由前蘇聯化學家齊齊巴賓（俄語：Алексей Евгеньевич Чичибабин）於1924年發現的利用醛合成吡啶的反應。齊齊巴賓吡啶合成反應中，三分子擁有α-氫的醛與一分子氨發生縮合，得到2,3,5-取代的吡啶。

反應機理

基本反應步驟

具體反應過程

下圖為該反應的詳細機理，其中示出了電子轉移方向、原子所帶電荷和各反應的類別。^[4]^[5]

參見

參考資料

^ A E Tscihtschibabin. Über Kondensation der Aldehyde mit Ammoniak zu Pyridinebasen. J. Prakt. Chem. 1924, 107: 122 [2009-10-05]. doi:10.1002/prac.19241070110. （原始內容存檔於2018-09-20）.
^ M Weiss. Acetic Acid—Ammonium Acetate Reactions. An Improved Chichibabin Pyridine Synthesis. Journal of the American Chemical Society. 1952, 74 (1): 200. doi:10.1021/ja01121a051.
^ Robert L. Frank, Raymond P. Seven. Pyridines. IV. A Study of the Chichibabin Synthesis. Journal of the American Chemical Society. 1949, 71 (8): 2629–2635. doi:10.1021/ja01176a008.
^ Li, J. J. Chichibabin pyridine synthesis. Name Reactions. 2009: 107–9. ISBN 3-540-40203-9. doi:10.1007/978-3-642-01053-8_51.
^ Weiss, M. Acetic Acid—Ammonium Acetate Reactions. An Improved Chichibabin Pyridine Synthesis. Journal of the American Chemical Society. 1952, 74 (1): 200–2. doi:10.1021/ja01121a051.

[1] A E Tscihtschibabin. Über Kondensation der Aldehyde mit Ammoniak zu Pyridinebasen. J. Prakt. Chem. 1924, 107: 122 [2009-10-05]. doi:10.1002/prac.19241070110. （原始內容存檔於2018-09-20）.

[2] M Weiss. Acetic Acid—Ammonium Acetate Reactions. An Improved Chichibabin Pyridine Synthesis. Journal of the American Chemical Society. 1952, 74 (1): 200. doi:10.1021/ja01121a051.

[3] Robert L. Frank, Raymond P. Seven. Pyridines. IV. A Study of the Chichibabin Synthesis. Journal of the American Chemical Society. 1949, 71 (8): 2629–2635. doi:10.1021/ja01176a008.

[JJLmech-4] Li, J. J. Chichibabin pyridine synthesis. Name Reactions. 2009: 107–9. ISBN 3-540-40203-9. doi:10.1007/978-3-642-01053-8_51.

[Weiss1952-5] Weiss, M. Acetic Acid—Ammonium Acetate Reactions. An Improved Chichibabin Pyridine Synthesis. Journal of the American Chemical Society. 1952, 74 (1): 200–2. doi:10.1021/ja01121a051.

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