Acetyldiarylamines by arylation of acetanilides. Some applications and limitations

Abstract

und Sodafabrik, West Germany. Triiron dodecacarbonyl was prepared according to literature.19 Photochemical Reaction of (-f)-a-Thujene (I) with Fe(CO)s.Irradiation was carried out for 1 h under nitrogen in petroleum ether (40-60 °C) solution using a Philips HPK-125 lamp in a water-cooled quartz immersion vessel. Reaction solutions of 1 g of I and 2.7 g of Fe(CO)s in ~300 mL of solvent were employed. The product mixture was filtered through Celite and the solution evaporated on a rotary evaporator. The residue (1.0 g) was washed with cold ether and recrystallized from tetrahydrofuran. The light yellow crystals of III melted at 106-107 °C, yield 62%.

Diarylamine/diarylnitroxide cycle: quantum chemical and electrochemical estimation

“…4,4′-bis(tert-butylphenyl)nitroxide was synthesized as described in [21]. Its identity was verified using ESR and UV-vis spectra.…”

Aromatic amines: use in azo dye chemistry

“…Otherwise the resultant -NH 3 + group would direct the incoming nitro group to the metaposition. The acetyl (Ac) group is removed following chlorination (12), upon heating the chlorinated intermediate in aqueous acid (H 3 O + ) or alkali in the final step of the reaction sequence.…”

“…It was proposed that the presence of a bulky alkyl/alkoxy group ortho to one of the -NH 2 groups prevented oxidation to reactive N-species (29). The absence of mutagenicity in benzene-based diamines 31 and 32 led to an extension of this approach to carcinogenic benzidines (11)(12)(13)(14). This work gave rise to the development of non-carcinogenic diamines 33 ( Figure 24) and their use in azo dye and pigment formation (30)(31).…”

Novel Synthetic Routes to Thienocarbazoles via Palladium‐ or Copper‐Catalyzed Amination or Amidation of Aryl Halides and Intramolecular Cyclization.

“…Thus, the amides 8 were converted to amines 4 and 5, obtained also as a mixture (,75% yield), using drastic basic conditions 18 by refluxing gently ethylene glycol (silicone bath at 2008C) (Scheme 4).…”

“…The amine 3 was obtained under drastic basic conditions 18 from the corresponding steric hindered acetamide 6 which was prepared by Beckmann rearrangement of the oxime of 6-acetylated compound 19 (Scheme 2). Attempts to perform the C -N coupling using the acetamide 6 under Buchwald's conditions were unsuccessfull.…”