Geminal Diazides Derived from 1,3-Dicarbonyls: A Protocol for Synthesis,The Journal of Organic Chemistry

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Geminal Diazides Derived from 1,3-Dicarbonyls: A Protocol for Synthesis
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2015-12-01 00:00:00 , DOI: 10.1021/acs.joc.5b02328
Hellmuth Erhardt ₁ , Andreas P. Häring ₁ , Andreas Kotthaus ₁ , Markus Roggel ₁ , My Linh Tong ₁ , Phillip Biallas ₁ , Martin Jübermann ₁ , Fabian Mohr ₂ , Stefan F. Kirsch ₁

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Geminal diazides constitute a rare class of compounds where only a limited number of methods are available for their synthesis. We present the reaction of 1,3-dicarbonyl compounds (as exemplified by malonates, 3-oxoesters, and 1,3-diketones) with molecular iodine and sodium azide in aqueous DMSO providing a general access to geminal diazides. A broad range of geminal diazides with various structural motifs including sterically demanding substituents and ordinary functional groups were synthesized, and it was shown that the diazidation of 1,3-dicarbonyls can be selectively achieved even in the presence of other 1,3-dicarbonyls with substituents at 2-position. Additionally, several diazides were studied regarding their thermal stability.

中文翻译：

1,3-二羰基衍生的二叠氮化物：合成规程

双叠氮化物是一类稀有的化合物，其中仅有限数量的方法可用于合成。我们介绍了1，3-二羰基化合物（以丙二酸酯，3-氧代酸酯和1,3-二酮为例）与分子碘和叠氮化钠在DMSO水溶液中的反应，提供了通向双叠氮化物的一般途径。合成了范围广泛的具有各种结构基序的双金属叠氮化物，包括空间上需要的取代基和普通官能团，结果表明，即使在存在其他1,3-二羰基的情况下，也可以选择性地实现1,3-二羰基的重氮化。 2位上的取代基。另外，研究了几种重氮化物的热稳定性。

更新日期：2015-12-01

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