Photolysis of open-chain 1,2-diazidoalkenes: generation of 2-azido-2H-azirines, formyl cyanide, and formyl isocyanide

Conformer-specific [1,2]H-tunnelling in captodatively-stabilized cyanohydroxycarbene (NC–C̈–OH)

“…Further pyrolysis products were HCN, CO, 8 , and 9 , as identified by comparison with reference spectra;11–14 8 has recently been detected in interstellar media 15. In addition, we also observed new unreported signals that we assign to 7t .…”

“…We assigned the slightly increasing signals at around 300–370 nm to 8 and 9 according to our observations in the IR spectra and through comparison with the literature and computations (Table S3 and S4†). 11…”

Synthesis of N-unsubstituted 1,2,3-triazoles via a cascade including propargyl azides, allenyl azides, and triazafulvenes

“…65 The competing secondary reactions of 3cc, electrocylic reaction to generate 4cc and sigmatropic isomerization to form 9, are similar to those of 3,4-diazidobuta-1,2-dienes, which were accessible as elusive intermediates by [3,3]-sigmatropic rearrangement of 1,4-diazidobut-2-ynes. In the latter cases, both electrocylization yielding NH-1,2,3-triazoles, 37 and alternatively a second sigmatropic shift to produce 2,3-diazidobuta-1,3-dienes [66][67][68] were previously reported. The diazide 2dd did not lead to unwanted side products; however, longer reaction times were necessary to prepare the bi-1,2,3-triazol-4-yl derivative 5dd.…”

An Efficient Oxidation of Primary Azides Catalyzed by Copper Iodide: A Convenient Method for the Synthesis of Nitriles

“…Recently, an interesting conversion of methyl arenes into aryl nitriles using phenyliodonium diacetate (PIDA) has been reported by Jiao and co-workers; [12] whilst the use of azides in the synthesis of nitriles has also been documented. [12,13] For example, conversion of organic azides into nitriles using bromine trifluoride was reported by Sasson and Rozen. [14] Furthermore, Chiba et al [15] reported the CÀC bond cleavage of a-azido carbonyl compounds to furnish nitriles and carboxylic acid.…”

“…[19] 2-(Azidomethyl)pyridine 1 l reacted smoothly to afford the corresponding nitrile 2 l in 53 % yield. [19] Aliphatic primary azides, [20] such as 1 m, 1 n, and 1 o reacted well to form the corresponding nitriles in good yields (70-73 %; Table 3, entries [12][13][14].…”