96227-78-0Relevant academic research and scientific papers
Synthesis, structure, and synthetic potential of arenediazonium trifluoromethanesulfonates as stable and safe diazonium salts
Filimonov, Victor D.,Krasnokutskaya, Elena A.,Kassanova, Assia Zh.,Fedorova, Valentina A.,Stankevich, Ksenia S.,Naumov, Nikolay G.,Bondarev, Alexander A.,Kataeva, Veronika A.
supporting information, p. 665 - 674 (2018/09/14)
Aromatic diazonium salts are valuable building blocks for organic synthesis; however, in most cases, they are unstable, unsafe, poorly soluble, and/or expensive. In this paper, we have shown that a variety of stable and safe arenediazonium triflates ArN2+ TfO– can be obtained easily and in high yields by diazotization of anilines with tert-butyl nitrite in the presence of trifluoromethanesulfonic acid. Arenediazonium triflates are relatively shelf-stable in the dry state. They dissolve well in water, as well as polar and even nonpolar organic solvents. Less than 800 J/g of energy is released during the thermal decomposition of these salts, which indicates their explosion safety. Arenediazonium triflates have a high reactivity in the known reactions of diazonium chemistry, and undergo an unusual metal-free chlorodediazonization reaction with chloroform and CCl4.
The sequel to a carbocyclic nucleoside synthesis: A divergent access to both arenediazonium ions and aryl triflates
Picherit,Wagner,Uguen
, p. 2579 - 2583 (2007/10/03)
Depending on the amount of acid used, treating aryl-dialkyl triazenes of general structure 3 with triflic acid resulted in the formation of either the corresponding arenediazonium triflates 4 or aryl triflates 8 apparently by two different pathways, the latter conversion being favoured at high acid concentration.
Development of a no-carrier-added method for 18F-labelling of aromatic compounds by fluorodediazonation
Knoechel, Arndt,Zwernemann, Olaf
, p. 325 - 336 (2007/10/03)
To improve the accessibility of [18F]arylfluorides a method is presented using the decomposition of aromatic diazonium salts in the presence of [18F]fluoride. Several p-toluidyldiazonium salts have been synthesized and decomposed in the presence of fluoride. The most useful salt, p-toluidyldiazomum-2,4,6-tri-isopropylbenzenesulfonate, has been used to investigate several parameters influencing the fluorination. No-carrier-added labelling with [18F]fluoride gave a radiochemical yield of 39% [18F]p-fluorotoluene in a total synthesis time of 78 minutes.
