Electronic effects on the amide E-/Z-preference of N-benzoyl-carbazole derivatives. Issue 22 (1st June 2016)

• Record Type: Journal Article
• Authors: Kayama, Susumu; Tani, Norihiko; Tabata, Hidetsugu; Oshitari, Tetsuta; Natsugari, Hideaki; Takahashi, Hideyo
• Is Part Of: Tetrahedron letters. Volume 57:Issue 22(2016)
• Page Start: 2395
• Page End: 2398
• Publication Date: 2016-06-01
• Subjects: Carbazole -- Amide -- Conformation -- Electronic effects; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2016.04.059
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Highlights: Amide conformers of N -benzoylated 3/4-substituted carbazoles distributed unequally. The ratio of the two conformers is controlled by the remote substituents. The electronic property of carbazole is the key factor. Abstract: N -2′, 4′, 6′-Trisubstituted 3-/4-substituted carbazole derivatives exist as mixtures of E -/ Z -amide conformers. It was found that the ratio of the two conformers is controlled by the electronic properties of the 3-/4-substituents. The 3-ammonium-6- t -butyl-carbazole derivative3s, in which the electronic character of each benzene ring of carbazole was properly tuned, provided the best preference for the Z -conformer ( E : Z = 1:2.50).