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请教高手,DPPA重排制备氨基的机理

时间: 2008-09-25 02:04:04 作者: 来源: 字号:
最近做一个化合物,间硝基苯乙胺采用间硝基苯丙酸以DPPA重排制备,其中以叔丁醇做溶剂,三乙胺做碱,其机理是什么啊?

DPPA can form acyl azide with acids, upon heating the acyl azide decomposes to generate acyl nitrene, which undergoes Curtis rearrangement to produce isocyanate. Tert-butanol is often used as solvent to trap this isocyanate to give BOC protected amine, which could be easily tranformed to the amine. Direct hydrolysis of the isocyanate gives some homo-urea (the condensation product between product amine and starting isocyanate).
反应先通过Curtius rearrangement由acyl azides变成isocyanates,接着当然就是醇(一般是用THF做溶剂的,醇是用来反应的,比如用乙醇也可以,只是用叔丁醇正好做成了Boc)对其加成,最后就是水解脱羧了。
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