The Chemistry of Vinyl, Allenyl, and Ethynyl Azides

Abstract

NaI 3 X = OH 4 X = Br 5 X = I Scheme 5.2 Synthesis of azidoquinones by nucleophilic substitution 3 O O O O O O Cl Cl

A novel oxidative transformation of alcohols to nitriles: an efficient utility of azides as a nitrogen source

“…Nevertheless, these reactions have paved new avenues of utility of azides in the synthesis of nitrogencontaining heterocyclic compounds by C-H or C-C bond cleavage. 5 The nitrile functionality is special in organic synthesis 6 as it occurs in several natural products 7 and can be transformed into a variety of functional groups such as amines, ketones, acids, amides etc. Aliphatic nitriles are synthesized using corresponding halides and metal cyanides, 8 whereas aromatic nitriles are synthesized by employing the classical Sandmeyer reaction.…”

Recent Organic Transformations with Silver Carbonate as a Key External Base and Oxidant

“…In 2014, the Bi group reported a Ag(I)-catalyzed hydroazidation to provide 2-azidoallyl alcohols 21 from ethynyl carbinols 20 (Scheme 15) [28]. Hydroazidation is one of the most attractive routes for synthesizing vinyl azides [29]. In a study of the effects of residual water in DMSO as the solvent (Scheme 16), dry DMSO provided a mixture of product 23 and TMS-protected product 23-TMS in a 1:3 ratio.…”

Synthesis, Characterization and Reactions of (Azidoethynyl)trimethylsilane

“…Whereas vinyl [1][2][3][4][5][6][7] and allenyl azides [7,8] are well-known for their manifold reactions and can be prepared by various methods, all attempts to isolate or even to simply detect ethynyl azides were unsuccessful until quite recently. The experimental pursuit of 1-azidoalk-1-ynes dates back to 1910 with the work of Forster and Newman [9]; however, like all other early attempts, only unwanted products were obtained, and no conclusive evidence for the formation of ethynyl azides or their secondary decay reactions was found [7,10].…”

“…The experimental pursuit of 1-azidoalk-1-ynes dates back to 1910 with the work of Forster and Newman [9]; however, like all other early attempts, only unwanted products were obtained, and no conclusive evidence for the formation of ethynyl azides or their secondary decay reactions was found [7,10]. This class of azides thus remained elusive for more than 100 years.…”