3- Phenylpyridine

If a clear solution of n-butyl-lithium is required for any purpose, it may be decanted through a glass wool plug as detailed under 2-Phenylpyridine, Note 4. 

The nitration of phenylpyridines and related compounds has attracted attention for a long time, and measurements of isomer proportions have been made for several compounds of this type. Nitration occurs in the phenyl ring. For 2-phenylpyridine and 2-phenylpyridine i-oxide measurements of the dependence of rate of nitration upon acidity in 75-81 % sulphuric acid at 25 °C show that both compounds are nitrated as their cations (table 8.1). The isomer distribution did not depend significantly upon the acidity, and by comparison with the kinetic data for quinolinium ( 10.4.2) the partial rate factors illustrated below were obtained.They should be compared with those for the nitration of 2-nitrobiphenyl ( 10.1). The protonated heterocyclic groups are much... 

Pyridine has been phenylated with the following free-radical sources benzenediazonium chloride with aluminum trichloride the Gomberg reaction " phenylhydrazine and metal oxides A -nitroso-acetanilide dibenzoyl peroxide phenylazotriphenylmethane di-phenyliodonium hydroxide and electrolysis of benzoic acid. ° Although 2-phenylpyridine usually accounts for over 50% of the total phenylated product, each of the three phenyl derivatives can be obtained from the reaction by fractional recrystallization of the... 

Oxazepines are readily decomposed by heat and light and by acids and bases.8 Some of these reactions proceed by hydrolytic opening of the oxazepine ring, as in the formation of 1-benzoylpyrrole (1) from 2-phenyl-l,3-oxazepine and cold dilute hydrochloric acid,12 while others involve valence-tautomeric oxazanorcaradienes, as in the thermal conversion of 2-phenyl-l,3-oxazcpine into 2-phenylpyridin-3-ol (2).12... 

In contrast to the above rearrangement reaction, the analogs 1 rearrange to 5-[(ethoxycarbonyl)-amino]-2-phenylpyridines 2 under thermal conditions.29 30... 

Phenylpyridine has been prepared in quantity only by heating phenyllithium with pyridine.2 The use of a sealed tube is avoided by replacing the ether with toluene.3... 

From this work the deactivation of pyridine to benzene was estimated as about 107. The partial rate factors for nitration of the 3 position of pyridine and the corresponding pyridinium ion were 101,7-2,5 and 1020 respectively. 2-Phenylpyridine was evaluated as 4.9 x 10"5 times less reactive than benzene. 

The partial rate factor for nitration of pyridine-N-oxide in the 4 position was estimated as 4x 10"6 which is, therefore, close to that found for the 3 position of pyridine, and 2-phenylpyridine-N-oxide was evaluated as 2xl0-4 times less reactive than benzene from rate measurements in 74.7-78.6 wt. % acid at 25 °C. 

Au( N) CI3 adducts are readily obtained by reaction of AU2CI6 or [ AuCU] with a variety of substituted heterocyclic ligands including 2-phenylpyridine [9], 2-benzylpyridines [10],... 

D., Yang, C.-T, Ranford, J.D., Vittal, J.J. and Lee, P.F. (2003) Synthesis, characterization, and biological activities of 2-phenylpyridine gold(lll) complexes with thiolate ligands. Dalton Transactions, (17), 3376. 

The most frequently reported mixed C/N-donor ligands are the 2-phenylpyridine anion, ppy (170), orthometalated 2,2 -bipyridine, C3N bpy (171), and derivatives, for example (172). 

Reactions of IrCL/I I2C) with 2-(/>-tolyl)pyridine(ptpy) and 3-methyl-2-phenylpyridine(mppy) gave [Ir(ptpy)2Cl]2 and [Ir(mppy)2Cl]2, respectively.323 Treatment with bpy afforded [Ir (ptpy)2-bpy]Cl and [Ir(mppy)2bpy]Cl. All complexes were characterized by UV-vis, emission spectroscopy, and cyclic voltammetry. 

A variety of transition metal complexes including organometallics was subjected to an ac electrolysis in a simple undivided electrochemical cell, containing only two current-carrying platinum electrodes. The compounds (A) are reduced and oxidized at the same electrode. If the excitation energy of these compounds is smaller than the potential difference of the reduced (A ) and oxidized (A ) forms, back electron transfer may regenerate the complexes in an electronically excited state (A+ + A A + A). Under favorable conditions an electrochemiluminescence (eel) is then observed (A A + hv). A weak eel appeared upon electrolysis o t]jie following complexes Ir(III)-(2-phenylpyridine-C, N ) [Cu(I)(pyridine)i],... 

With regard to transition metal complexes thg+majority of eel studies have been carried out with RuCbipy) and its derivatives (11, 20-33). Recently, King, Spellane, and Watts reported on the mission properties of Ir(ppy) with ppy = 2-phenylpyridine-C, N (41 ) which can be gonsidered to be an organometallic counterpart of Ru(bipy) ... 

---