Nierenstein反應
外觀
Nierenstein反應(Nierenstein reaction)
![Nierenstein反應](http://upload.wikimedia.org/wikipedia/commons/thumb/f/f0/NierensteinReaction.png/320px-NierensteinReaction.png)
反應機理[編輯]
反應機理與Arndt-Eistert反應類似,即酰氯與重氮甲烷縮合為重氮酮中間體,然後重氮酮發生質子化、放出氮氣得到產物。
![Nierenstein反應機理](http://upload.wikimedia.org/wikipedia/commons/thumb/f/fd/NierensteinMechanism.png/420px-NierensteinMechanism.png)
以苯乙酰氯合成苄基氯甲基酮時,需要通入氯化氫氣體才能使重氮酮轉化為鹵代酮產物。[3]
應用[編輯]
1、Nierenstein (1924) 最初發現的反應:[4]
![Nierenstein 1924](http://upload.wikimedia.org/wikipedia/commons/thumb/4/47/Nierenstein1924.png/420px-Nierenstein1924.png)
2、以苯甲酰溴為原料,反應後得到溴甲酰苯及環狀二噁烷二聚體[5]
![Nierenstein 1924](http://upload.wikimedia.org/wikipedia/commons/thumb/0/03/NierensteinDimer.png/420px-NierensteinDimer.png)
參見[編輯]
參考資料[編輯]
- ^ Clibbens, D.; Nierenstein, M. The action of diazomethane on some aromatic acyl chlorides. J. Chem. Soc. 1915, 107: 1491. doi:10.1039/CT9150701491.
- ^ Bachman, W. E.; Struve, W. S. Org. React. 1942, 1: 38. 缺少或
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為空 (幫助)(綜述) - ^ McPhee, W. D; Klingsberg, E. Organic Syntheses, Coll. Vol. 3, p.119 (1955); Vol. 26, p.13 (1946). (Article (頁面存檔備份,存於網際網路檔案館))
- ^ M. Nierenstein, D. G. Wang, and J. C. Warr. The Action of Diazomethane on some Aromatic Acyl Chlorides II. Synthesis of Fisetol. J. Am. Chem. Soc. 1924, 46 (11): 2551–2555. doi:10.1021/ja01676a028.
- ^ H. H. Lewis, M. Nierenstein, and Enid M. Rich. The Action of Diazomethane on some Aromatic Acyl Chlorides III. The Mechanism of the Reaction. J. Am. Chem. Soc. 1925, 47 (6): 1728–1732. doi:10.1021/ja01683a036.