259826-43-2Relevant academic research and scientific papers
Oxidation of azides by the HOF·CH3CN: A novel synthesis of nitro compounds
Carmeli, Mira,Rozen, Shlomo
, p. 4585 - 4589 (2007/10/03)
The HOF·CH3CN complex, readily prepared by passing F 2 through aqueous acetonitrile, is an exceptionally efficient oxygen transfer agent. It is unique in its capacity to oxidize various azides into the corresponding nitro derivatives. This method requires short reactions times and room temperature or below, and the desired nitro compounds were usually isolated in very good yields. The respective nitroso derivatives are believed to be the intermediates in this reaction. Functional groups such as aromatic rings, ketones, nitriles, halides, alcohols, and esters are tolerated. Sulfides react with HOF·CH3CN usually at the same rate as azides. Amines and olefins, however, react faster, so they have to be protected first. Nitro derivatives with various oxygen isotopes can be made using the labeled H 18OF·CH3CN. In the case of chiral azides the stereochemistry around the nitrogen-bonded carbons is retained.
Nicotinoyl azide (NCA)-mediated Mitsunobu reaction: An expedient one-pot transformation of alcohols into azides
Papeo, Gianluca,Posteri, Helena,Vianello, Paola,Varasi, Mario
, p. 2886 - 2892 (2007/10/03)
A practical and simple method that allows preparation of azides from alcohols is described. The process involves oxyphosphonium-type activation and it is based upon the use of nicotinoyl azide (NCA), a cheap and easily accessible azide ion source.
A simple and convenient synthesis of alkyl azides under mild conditions
Ito,Koyakumaru,Ohta,Takaya
, p. 376 - 378 (2007/10/02)
Various primary and secondary alkyl azides have been synthesized in high yields by the fluoride anion induced S(N)2 substitution reactions of the corresponding alkyl halides, phosphates, or tosylates and trimethylsilyl azide.
Zinc Azide Mediated Mitsunobu Substitution. An Expedient Method for the One-Pot Azidation of Alcohols
Viaud, Marie Claude,Rollin, Patrick
, p. 130 - 132 (2007/10/02)
In the presence of the diisopropyl azodicarboxylate/triphenylphosphine couple, alcohols react with zinc azide/bis-pyridine complex to give various azides via a Mitsunobu-type substitution.
