Reactions with Geminal Diazides: Long Known, Full of Surprises, and New Opportunities

Abstract Geminal diazides are uncommon yet powerful tools in organic synthesis. The chemistry of this class of functional compounds is characterized by quite unusual reactivities, including fragmentations and degradations, along with known reactions of organic azides. This Short Review highlights the major reactivities of various structural units having geminal diazido moieties, and provides an overview on the synthetic opportunities of such compounds. 1 Introduction 2 Preparation of Geminal Diazides 3 Reactivities of Geminal Diazides 3.1 α,α-Diazido Carbonyls 3.2 1,3-Diketones 3.3 Diazidated β-Ketoesters 3.4 Diazidated Malonates 3.5 Diazidated Malonamides 3.6 Miscellaneous Geminal Diazides 4 Conclusion