23873-81-6Relevant articles and documents
Synthesis of a stereochemically defined 1,2-diazetine N,N′-dioxide and a study of its thermal decomposition
Breton, Gary W.,Oliver, Lindsey H.,Nickerson, Justine E.
, p. 1412 - 1416 (2007)
(Chemical Equation Presented) Diazetine dioxide 1a has been synthesized in a single step via oxidation of meio-2,3-diphenyl-1,2-ethanediamine with dimethyldioxirane, albeit in low yield (7%). Thermal decomposition of 1a afforded predominantly either trans-stilbene or diphenyl glyoxime depending on solvent, temperature, and the presence of an amine catalyst. Reaction in chloroform at 69°C favored elimination of NO and formation of trans-stilbene. The stereospecific formation of trans-stilbene suggests a mechanism of decomposition in which C-N bond cleavage leads to a diradical intermediate stabilized by the phenyl group. Bond rotation followed by cleavage of the second C-N bond accounts for the trans-stilbene. At 25 °C in chloroform, while trans-stilbene was still the major product, some diphenyl glyoxime was also observed (4% yield). However, la as a solution in chloroform in the presence of Et3N, or 1a as a solution in DMSO-d6, afforded predominantly diphenyl glyoxime. These results are interpreted in terms of two closely competing reactions subject to the effects of entropic contributions.
Novel riboflavin-inspired conjugated bio-organic semiconductors
Richtar, Jan,Heinrichova, Patricie,Apaydin, Dogukan Hazar,Schmiedova, Veronika,Yumusak, Cigdem,Kovalenko, Alexander,Weiter, Martin,Sariciftci, Niyazi Serdar,Krajcovic, Jozef
, (2018/09/12)
Flavins are known to be extremely versatile, thus enabling routes to innumerable modifications in order to obtain desired properties. Thus, in the present paper, the group of bio-inspired conjugated materials based on the alloxazine core is synthetized using two efficient novel synthetic approaches providing relatively high reaction yields. The comprehensive characterization of the materials, in order to evaluate the properties and application potential, has shown that the modification of the initial alloxazine core with aromatic substituents allows fine tuning of the optical bandgap, position of electronic orbitals, absorption and emission properties. Interestingly, the compounds possess multichromophoric behavior, which is assumed to be the results of an intramolecular proton transfer.
Synthesis and characterization of 2,3,5,6-tetraphenylpyrazine-N, N-dioxide: New nitrone dimer species
Essa, Ali Hashem,Al-Shamkhani, Zeki A. Nasir,Jalbout, Abraham F.,Hameed, Ali Jameel
experimental part, p. 2235 - 2242 (2011/04/17)
The synthesis, characterization and physical properties of 2,3,5,6-tetraphenylpyrazine-N,N-dioxide presently are reported. A specific reduction mechanism of an oxime using zinc with NH4Cl to yield hydroxylamine was performed. This was followed by a condensation reaction with sulfuric acid that leads to 2,3,5,6-tetraphenylpyrazine-N,N-dioxide. The product was characterized by means of IR, UV,1H-NMR and13C-NMR spectroscopy which were complemented by theoretical computations. The Japan Institute of Heterocyclic Chemistry.
