title: Geminal Diazides Derived from 1,3-Dicarbonyls: A Protocol for Synthesis.
abstract: 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.
authors.affiliation: Organic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany.
authors.forename: Hellmuth
authors.initials: H
authors.lastname: Erhardt
authors.affiliation: Organic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany.
authors.forename: Andreas P
authors.initials: AP
authors.lastname: Häring
authors.affiliation: Organic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany.
authors.forename: Andreas
authors.initials: A
authors.lastname: Kotthaus
authors.affiliation: Organic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany.
authors.forename: Markus
authors.initials: M
authors.lastname: Roggel
authors.affiliation: Organic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany.
authors.forename: My Linh
authors.initials: ML
authors.lastname: Tong
authors.affiliation: Organic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany.
authors.forename: Phillip
authors.initials: P
authors.lastname: Biallas
authors.affiliation: Organic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany.
authors.forename: Martin
authors.initials: M
authors.lastname: Jübermann
authors.affiliation: Inorganic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany.
authors.forename: Fabian
authors.initials: F
authors.lastname: Mohr
authors.affiliation: Organic Chemistry, Bergische Universität Wuppertal , Gaußstraße 20, 42119 Wuppertal, Germany.
authors.forename: Stefan F
authors.initials: SF
authors.lastname: Kirsch