76241-81-1Relevant articles and documents
Selective Zincation of 1,2-Dicyanobenzene and Related Benzonitriles in Continuous Flow Using in Situ Trapping Metalations
Ketels, Marthe,Ziegler, Dorothée S.,Knochel, Paul
, p. 2817 - 2822 (2017)
A mild and general metalation procedure for the functionalization of 1,2-dicyanobenzene and related polyfunctionalized benzonitriles using a commercially available continuous flow setup is reported. The addition of TMPLi (TMP = 2,2,6,6-tetramethylpiperidy
Carbopalladation of nitriles: Synthesis of 2,3-diarylindenones and polycyclic aromatic ketones by the Pd-catalyzed annulation of alkynes and bicyclic alkenes by 2-iodoarenenitriles
Pletnev, Alexandre A.,Tian, Qingping,Larock, Richard C.
, p. 9276 - 9287 (2007/10/03)
2-Iodobenzonitrile, its derivatives, and various heterocyclic analogues undergo palladium(O)-catalyzed annulation onto diarylacetylenes or bicyclic alkenes to afford 2,3-diarylindenones and polycyclic aromatic ketones in very good to excellent yields. This reaction represents one of the first examples of the addition of an organopalladium moiety to the carbon-nitrogen triple bond of a nitrile. The reaction is compatible with a number of functional groups. A reaction mechanism, as well as a model accounting for the electronic effects of substituents on the aromatic ring of the nitrile, is proposed.
Vibrational spectra of halophthalonitriles
Halls, Mathew D.,Aroca, Ricardo,Terekhov, Dmitri S.,D'Ascanio, Anna,Leznoff, Clifford C.
, p. 305 - 317 (2007/10/03)
The fundamental vibrational modes of a series of six halophthalonitriles have been studied using Raman and infrared spectroscopy. The vibrational assignment of experimental wave numbers obtained from solid samples was aided using quantum chemical computations. Semi-empirical methods and the local SVWN functional were used to obtain vibrational wave numbers and atomic displacement representations of the fundamental molecular vibrations. The study of a series of molecules with similar structure permits the identification of characteristic wave numbers and the effect of the halosubstitution in the molecular structure.
Multisubstituted phthalonitriles, naphthalenecicarbonitriles, and phenanthrenetetracarbonitriles as precursors for phthalocyanide syntheses
Leznoff, Clifford C.,Terekhov, Dmitri S.,McArtur, Colin R.,Vigh, Steven,Li, Jing
, p. 435 - 443 (2007/10/02)
Electrophilic aromatic nitration under mild conditions of 4-hydroxyphthalonitrile gave 4-hydroxy-3-nitrophthalonitrile and 4-hydroxy-5-nitrophthalonitrile, while bromination yielded 3-bromo-4-hydroxyphthalonitrile, 4-bromo-5-hydroxyphthalonitrile, and 3,5-dibromo-4-hydroxyphthalonitrile.Iodination gave 4-hydroxy-5-iodophthalonitrile and 4-hydroxy-3,5-diiodophthalonitrile.Coupling of 4-iodophthalonitrile, 3-iodophthalonitrile, and 5-iodo-2,3-dicyanonaphthalene with trans-1,2-bis(tri-n-butylstannyl)ethene gave trans-1,2-bis(3,4-dicyanophenyl)ethene, trans-1,2-bis(2,3-dicyanophenyl) ethene, and trans-1,2-bis(6,7-dicyanonaphthyl)ethene.Photocyclization of a dilute solution of cis-or trans-1,2bis(3,4-dicyanophenyl)ethene in dioxane gave a 1:1 mixture of 2,3,6,7- and 2,3,5,6,-tetracyanophenanthrenes separable by chromatography.Key words: phthalonitriles, naphthalenedicarbonitriles, phenanthrenetetracarbonitriles, electrophilic substitution.
