Back to Search
Start Over
Oxidative Dimerization of Triarylamines Promoted by WCl6, Including the Solid State Isolation and the Crystallographic Characterization of a Triphenylammonium Salt.
- Source :
-
Inorganic Chemistry . 1/19/2016, Vol. 55 Issue 2, p887-893. 7p. - Publication Year :
- 2016
-
Abstract
- The triphenylammonium salt [NHPh3][WCl6], 1, and the product of the C-C dimerization of triphenylamine, Ph2N(C6H4)2NPh2, 2, were afforded from the reaction between WCl6 and NPh3 in CH2Cl2. Compound 2 was isolated in 43% yield upon hydrolysis of the reaction mixture. The X-ray structure of 1 provides the first crystallographic characterization of the triphenylammonium ion. Combined EPR and DFT studies gave insight into the reaction mechanism, and allowed the identification of WCl5•••[Cl(C6H4)NPh2] as a presumable key intermediate. The reactions of WCl6 with 4-bromotriphenylamine, 4,4′-dimethyltriphenylamine, 9-phenylcarbazole, followed by hydrolytic treatment, led to the dimerization products 3-6, in admixture with variable amounts of the parent amines. N,N,N′,N′-tetrakis(4-bromophenyl)-[1,1′-biphenyl]-4,4′-diamine, 3, was isolated in 60% yield from the reaction of WCl6 with 4,4′-dibromotriphenylamine. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00201669
- Volume :
- 55
- Issue :
- 2
- Database :
- Academic Search Index
- Journal :
- Inorganic Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 112935967
- Full Text :
- https://doi.org/10.1021/acs.inorgchem.5b02392