32494-23-8Relevant articles and documents
Unexpected outcome in the reaction of triazolinedione with carbon nanotubes
Menard-Moyon, Cecilia,Gross, Marius,Bernard, Maxime,Turek, Philippe,Doris, Eric,Mioskowski, Charles
, p. 4817 - 4819 (2007)
The reactivity of triazolinedione (TAD) was investigated in the Diels-Alder reaction with carbon nanotubes. However, an unexpected conversion of TAD into its deaza dimer was observed. ESR spectroscopy suggested that the process was initiated by electron t
Triazolinediones. Conversion to Deaza Dimers by Electron-Transfer Catalysis. A Possible Radical Anion Diels-Alder Reaction
Borhani, David W.,Greene, Frederick D.
, p. 1563 - 1570 (2007/10/02)
1,2,4-Triazolidines, 4-RTAD (1), are converted to dimeric products (deaza dimers 2) with loss of dinitrogen by a variety of agents of which the most effective are good single-electron donors (sodium naphthalenide, sodium iodide, sodium metal).The reaction is retarded by tetracyanoethylene or lead tetraacetate (electron acceptors).A radical anion chain reaction is proposed (Scheme IV and eq 9-12) in which the overall result is the reaction of two RTAD --> deaza dimer 2 + N2, catalyzed by electron donors.The sequence suggested includes the cycloaddition of RTAD anion radical with the dienophile RTAD, the first example (of which we are aware) of a radical anion Diels-Alder reaction.In the presence of an alcohol (e.g., methanol) PhTAD is converted, again in a catalyzed reaction (e.g., sodium iodide), to a methanol addition product, formulated as 3a (eq 5a, 15, and 17 and Scheme V).
Reaction of Electron-Deficient 1,2,4-Triazoline-3,5-diones with Electron-Rich Nitrogen Heterocycles
Hall, J. Herbert,Kaler, Lauren,Herring, Roger
, p. 2579 - 2582 (2007/10/02)
The reaction of 4-substituated 1,2,4-triazoline-3,5-diones (RTAD's) with some electron-rich nitrogen heterocycles has been examined.RTAD's react rapidly with 1-methylindole to give aromatic disubstitution in the 2- and 3-positions along with some polymer.