493-77-6Relevant articles and documents
Diverse reactivity of rhodium β-(tetraphenyl)tetraphenyl porphyrin chlorides with benzonitrile: Formation of Rh porphyrin arene and imine complexes
Zhou, Xiang,Tse, Man Kin,Wu, De-Dong,Mak, Thomas C.W.,Chan, Kin Shing
, p. 80 - 86 (2000)
The reaction of rhodium trichloride with β-(tetraphenyl)tetraphenyl porphyrin, H2(tpp)(Ph)4, and β-(tetraphenyl)tetrakismesityl porphyrin, H2(tmp)(Ph)4, in refluxing benzonitrile gave novel rhodium porphyrin chl
Metalation of 2-Methyl-N-phenylbenzamide with n-Butyllithium. Formation of N,3-Diphenyl-1-isoquinolinamine by Subsequent Reaction with Benzonitrile
Abraham, Tonson
, p. 371 - 374 (1982)
2-Methyl-N-phenylbenzamide was metalated with two equivalents of n-butyllithium.Benzonitrile was allowed to react with the organomethallic intermediate thus formed to yield N,3-diphenyl-1-isoquinolinamine. - Keywords: Benzamide, iminophenylethyl-phenyl; Cyclodehydratation; Isoquinolinamine, diphenyl; Lithiation
Direct Synthesis of a Covalent Triazine-Based Framework from Aromatic Amides
Yu, Soo-Young,Mahmood, Javeed,Noh, Hyuk-Jun,Seo, Jeong-Min,Jung, Sun-Min,Shin, Sun-Hee,Im, Yoon-Kwang,Jeon, In-Yup,Baek, Jong-Beom
, p. 8438 - 8442 (2018)
There have been extensive efforts to synthesize crystalline covalent triazine-based frameworks (CTFs) for practical applications and to realize their potential. The phosphorus pentoxide (P2O5)-catalyzed direct condensation of aromatic amide instead of aromatic nitrile to form triazine rings. P2O5-catalyzed condensation was applied on terephthalamide to construct a covalent triazine-based framework (pCTF-1). This approach yielded highly crystalline pCTF-1 with high specific surface area (2034.1 m2 g?1). At low pressure, the pCTF-1 showed high CO2 (21.9 wt % at 273 K) and H2 (1.75 wt % at 77 K) uptake capacities. The direct formation of a triazine-based COF was also confirmed by model reactions, with the P2O5-catalyzed condensation reaction of both benzamide and benzonitrile to form 1,3,5-triphenyl-2,4,6-triazine in high yield.
Domino reaction of lithiated allenes with nitriles
Langer, Peter,Doering, Manfred,Seyferth, Dietmar
, p. 1927 - 1928 (1998)
Addition of nitriles to dilithiated allenes results in a unique domino cyclization which involves the so far highest number of nitrile molecules added to an organolithium reagent to form unambiguously characterized oligomers.
Butyllithium-induced Cyclotrimerisation Reactions of Organic Nitriles: Solvent Dependency, Crystal and Solution Structures of Lithio Triazine Intermediates and an Unexpected Rearrangement of Dihydrotriazino Anions
Armstrong, David R.,Clegg, William,MacGregor, Murray,Mulvey, Robert E.,O'Neil, Paul A.
, p. 608 - 610 (1993)
Sequential addition of ButCN and PhCN (2 equiv.) to BunLi in the presence of tetrahydrofuran (THF) produces an isolable lithio 1,4-dihydrotriazine tris(THF) solvate, characterised by both NMR spectroscopic and X-ray crystallographic methods, which converts to a 1,2-dihydro arrangement on methanolysis.
Direct synthesis of covalent triazine-based frameworks (CTFs) through aromatic nucleophilic substitution reactions
Chen, Tao,Li, Wen-Qian,Hu, Wei-Bo,Hu, Wen-Jing,Liu, Yahu A.,Yang, Hui,Wen, Ke
, p. 18008 - 18012 (2019)
Despite extensive efforts, only three main strategies have been developed to synthesize covalent triazine-based frameworks (CTFs) thus far. We report herein a totally new synthetic strategy which allows C-C bonds in the CTFs to be formed through aromatic nucleophilic substitution reactions. The as-synthesized CTF-1 and CTF-2 exhibited photocatalytic water splitting activity comparable to the CTFs made using ionothermal or Br?nsted acid-catalyzed polymerization. Interestingly, CTF-2 distinguished itself by its two-photon fluorescence (emission at ～530 nm under irradiation at either 400 nm or 800 nm).
Functionalized fluorenes via dicationic electrophiles
Stentzel, Michael R.,Klumpp, Douglas A.
, p. 1675 - 1677 (2019)
Dicationic fluorenyl cations are shown to react with nitriles to provide amide-functionalized fluorenes. A similar reaction with alcohols gives ether derivatives. The chemistry is initiated by the reactions of N-heterocyclic ketones in a superacidic solution. This leads to cyclizations involving 2-biphenyl groups and formation of the reactive fluorenyl cations.
Reactions of rac-(ebthi)M(η2-Me3SiC2SiMe3) (M=Ti, Zr) with Aryl Nitriles
Becker, Lisanne,Arndt, Perdita,Spannenberg, Anke,Rosenthal, Uwe
, p. 12595 - 12600 (2014)
The reactions of the Group 4 metallocene alkyne complexes rac-(ebthi)M(η2-Me3SiC2SiMe3) (1 a: M=Ti, 1 b: M=Zr; rac-(ebthi)=rac-1,2-ethylene-1,1′-bis(η5-tetrahydroindenyl)) with Ph C N were investigated. For 1 a, an unusual nitrile–nitrile coupling to 1-titana-2,5-diazacyclopenta-2,4-diene (2) at ambient temperature was observed. At higher temperature, the C C coupling of two nitriles resulted in the formation of a dinuclear complex with a four-membered diimine bridge (3). The reaction of 1 b with Ph C N afforded dinuclear compound 4 and 2,4,6-triphenyltriazine. Additionally, the reactivity of 1 b towards other nitriles was investigated.
Synthetic and theoretical MO calculational studies of lithiotriazine intermediates produced during alkyllithium-induced cyclotrimerisation reactions of organic nitriles, and comparison of their structures with that of a methylmagnesiotriazine derivative
Armstrong, David R.,Henderson, Kenneth W.,MacGregor, Murray,Mulvey, Robert E.,Ross, Michael J.,et al.
, p. 79 - 94 (1995)
Benzonitrile can be readily cyclotrimerised by treatment with a suitable alkyllithium to give a simple triazine or to a solvated lithiodihydrotriazine derivative.Which cyclic product dominates depends mainly on the source of the active Li+ cation (n-butyllithium, t-butyllithium and tetramethylguanidinolithium are considered here), and on the solvent employed.X-ray crystallographic studies on a representative compound show that the lithio species exists as a mononuclear, contact ion pair structure, with the triazine ring in a 1,4-dihydro state.On reaction with theGrignard reagent, MeMgCl, this compound gives a methylmagnesiodihydrotriazine, which has also been crystallographically characterised and found to closely resemble its lithio precursor.Ab initio MO calculations on model systems reveal that the 1,4-dihydrotriazine arrangements is energetically preferred to the 1,2-dihydro alternative irrespective of the counterion (Li+ or H+) present.A theoretical investigation of the methanolysis of the lithio species indicates that the formation of an intermediate MeOH complex, with the alcohol attached to a ring N atom and not to Li+, directs the reaction towards ultimate formation of a 1,2-dihydrotriazine.Keywords: Triazine; Lithium; Magnesium; Ab initio; Crystal structure
Reactions of benzene derivatives containing C≡N and C≡CH groups with atomic chromium
Vasil'kov,Pribytkov,Peregudov
, p. 149 - 153 (1997)
Reactions of benzonitrile and phenylacetylene with atomic chromium were studied. Products of the trimerization and polymerization of the initial aromatic compounds form in considerable amounts along with bisarenechromium complexes. Mechanisms of the reactions were suggested. The possibility of increasing the yields of the bisarenechromium complexes was considered.
