Synthesis and structure of Meisenheimer adducts in nucleophilic aromatic amination of 4,6-dinitrobenzofuroxan

Mechanism of Trifluoromethylation of Aryl Halides with CuCF3 and the Ortho Effect

“…A crude yet informative estimate of the magnitude of π-conjugation in [A]­TS 1 can be obtained from some reported structural data. The C–N bond distance of 1.45 Å in [A]­TS 1 for p -NO 2 C 6 H 4 I is longer than in the Meisenheimer complexes and Domenicano’s classical quinoid-like structure of p -nitroaniline (1.434(2) Å), , yet comparable to that in p -nitroanisole (1.450(6) Å) with substantial cross-conjugation of the MeO (+M) and NO 2 (−M) groups. The reaction center in [A]­TS 1 is therefore undoubtedly influenced by resonance effects of substituents R on the ring, i.e., exactly the case where σ p – rather than σ p should be used for Hammett-type correlations .…”

“…Highly informative intimate details of the AOARE process are revealed by the structure of the OA transition state [A]­TS 1 . Although care should be exercised when comparing intermediates and transition states, it might be useful, in this particular case, to juxtapose [A]­TS 1 with structurally characterized Meisenheimer complexes . The benzene ring in Meisenheimer intermediates conventionally adopts a sofa conformation, and a roughly tetrahedral geometry is observed at the sp 3 -hybridized ipso carbon.…”

Synthesis and Antimicrobial Activity of Bis-4,6-sulfonamidated 5,7-Dinitrobenzofuroxans

“…Recently, research and development in the medicinal chemistry field have produced hybrid compounds in which benzofuroxanyl moieties are present in a single molecule together with classical drug moieties. Consequently, new antiulcer drugs, calcium channel modulators, vasodilator derivatives, antioxidants, and others have been described and are currently under study [13][14][15][16][17][18][19]. On the other hand, these kinds of compound have also been reported as components in primary explosives, polymers, and propellants [8,[20][21][22].…”