Nierenstein反应
外观
Nierenstein反应(Nierenstein reaction)
![Nierenstein反应](http://upload.wikimedia.org/wikipedia/commons/thumb/f/f0/NierensteinReaction.png/320px-NierensteinReaction.png)
反应机理
[编辑]反应机理与Arndt-Eistert反应类似,即酰氯与重氮甲烷缩合为重氮酮中间体,然后重氮酮发生质子化、放出氮气得到产物。
![Nierenstein反应机理](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时,需要通入氯化氢气体才能使重氮酮转化为卤代酮产物。[3]
应用
[编辑]1、Nierenstein (1924) 最初发现的反应:[4]
![Nierenstein 1924](http://upload.wikimedia.org/wikipedia/commons/thumb/4/47/Nierenstein1924.png/420px-Nierenstein1924.png)
2、以苯甲酰溴为原料,反应后得到溴甲酰苯及环状二噁烷二聚体[5]
![Nierenstein 1924](http://upload.wikimedia.org/wikipedia/commons/thumb/0/03/NierensteinDimer.png/420px-NierensteinDimer.png)
参见
[编辑]参考资料
[编辑]- ^ 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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为空 (帮助)(综述) - ^ McPhee, W. D; Klingsberg, E. Organic Syntheses, Coll. Vol. 3, p.119 (1955); Vol. 26, p.13 (1946). (Article (页面存档备份,存于互联网档案馆))
- ^ 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.