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Geminal Diazides Derived from 1,3-Dicarbonyls: A Protocol for Synthesis

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https://figshare.com/articles/dataset/Geminal_Diazides_Derived_from_1_3_Dicarbonyls_A_Protocol_for_Synthesis/2097454
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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.
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2016-02-12
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