Reaction of 2,3-Diphenylindole with Permanganate. Rearrangements of N,N′-Dimers

Abstract

Based on spectroscopic and chemical evidence dimeric structure 1 is assigned to the major product from reaction of 2,3-diphenylindole and potassium permanganate. Thermal and acid-catalyzed rearrangements of N,N′-dimers 1 and 6 were studied.

Analysis of Interconversion between Atropisomers of Chiral Substituted 9,9’‐Bicarbazole

“…The energies of two molecules of the carbazolyl radical 5 • were also calculated [roB3LYP/6‐31G(d)] (Figure 2), since 9,9’‐bicarbazole is known to undergo thermal N−N bond cleavage [6] . The energy was calculated to be 135.3 kJ/mol, which is lower than the energies of the trans transition states of interconversion.…”

Schischkiniin support studies: synthetic access to 1,1′-bisindoles

“…1 Although the 1,1 0 -bisindole moiety was observed in an hypothetical intermediate during the oxidation of 3-indoleacetic acid over 60 years ago, 3,4 syntheses of this heterocyclic motif are sparse (4 synthetic examples). [5][6][7][8][9] 2,3-Diphenylindole and N-hydroxyindole-3-carboxylic acid can be converted to their respective 1,1 0 -bisindoles with hydroiodic acid 5,6 and a rare earth metal complex has been used to effect dimerization of indole to 1,1 0 -bisindole. 7 In the only example of a 1,1 0 -bisindole that does not rely on the dimerization of a preconstructed indole, 2-phenyl-1,1 0bisindole has been synthesized by the palladium-catalyzed domino reaction of a 2-bromophenylacetylene with 1-aminoindole.…”

Antimicrobial Activity of N‐Substituted Derivatives of 5‐Chloro‐2,3‐ Diphenyl Indole

“…According to an early study, precursor 1 was oxidized by KMnO 4 in accordance with the conditions of the early V. Dave's approach, [41] giving the corresponding dimeric structure 6 (Scheme 1). This is because the dimer 2,2′,3,3′‐tetraphenyl‐1,1′‐biindole is considered to be the major product of the reaction of 2,3‐diphenyl indole and potassium permanganate.…”