20544-50-7Relevant academic research and scientific papers
Synthesis of Geminal Azido-Halo Compounds and α-Azidoalkyl Esters from Aldehydes via α-Azido Alcohols
Banert, Klaus,Berndt, Christian,Weigand, Kevin
, p. 4900 - 4903 (2017)
α-Azido alcohols are generated by treating aldehydes with hydrazoic acid in chloroform. These adducts are transformed into geminal azido-halo compounds through the reaction with phosphorus trichloride or phosphorus tribromide, whereas α-azidoalkyl esters are isolated after interaction with acyl chlorides.
Ring Enlargement of Three-Membered Heterocycles by Treatment with In Situ Formed Tricyanomethane
Banert, Klaus,Chityala, Madhu,Korb, Marcus
, p. 6158 - 6164 (2020/05/04)
Although the chemistry of elusive tricyanomethane (cyanoform) has been studied during a period of more than 150 years, this compound has very rarely been utilized in the synthesis or modification of heterocycles. Three-membered heterocycles, such as epoxides, thiirane, aziridines, or 2H-azirines, are now treated with tricyanomethane, which is generated in situ by heating azidomethylidene-malonodinitrile in tetrahydrofuran at 45 °C or by adding sulfuric acid to potassium tricyanomethanide. This leads to ring expansion with formation of 2-(dicyanomethylidene)oxazolidine derivatives or creation of the corresponding thiazolidine, imidazolidine, or imidazoline compounds and opens up a new access to these push–pull-substituted olefinic products. The regio- and stereochemistry of the ring-enlargement processes are discussed, and the proposed reaction mechanisms were confirmed by using 15N-labeled substrates. It turns out that different mechanisms are operating; however, tricyanomethanide is always acting as a nitrogen-centered nucleophile, which is quite unusual if compared to other reactions of this species.
Synthesis of aryl azides and vinyl azides via proline-promoted CuI-catalyzed coupling reactions.
Zhu, Wei,Ma, Dawei
, p. 888 - 889 (2007/10/03)
The coupling reaction of aryl halides or vinyl iodide with sodium azide under catalysis of CuI/L-proline works at relatively low temperature to provide aryl azides or vinyl azides in good to excellent yields.
Regioselective ring opening of silyl epoxy alcohols with azide ion
Chakraborty,Reddy
, p. 1335 - 1338 (2007/10/02)
Presence of silyl group on epoxy ring allows azide ion to open 2,3-epoxy alcohols exclusively at the silicon bearing carbon.
Cathodic Reduction of Aliphatic Azides and of Azides, Activated by Olefinic and Carbonyl Groups
Knittel, Dierk
, p. 679 - 688 (2007/10/02)
In the majority of compounds investigated the main reduction path starting from azido compounds under parotic conditions leads to the retainment of one nitrogen in the product molecules, provided an initial phase of consumption of residual water is overcome.Good to excellent yields of N-acylated or nicely stable N,N-diacetylated aminoderivatives are obtainable.Even a secondary position of the original N3-group prevents diacetylation completely by steric reasons.Vicinal halogen cause the loss of all nitrogen atoms as does the presence of H+ in the case of azidocarbonyl compounds.Where reduction potential of the starting azide lies within the reduction range of Ac2O even high chemical yields of aminoderivatives are obtainable but with decrease of current efficiency.Reductive acetylation of benzoyl azide leads to the isolation of both rotational isomers of N-acetylbenzamide. - Keywords: Unsaturated Azides and Amines; α-Azido- and α-Aminocarbonylcompounds; Cathodic reduction
