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