Nitrosation of m-xylene, anisole, 4-nitrophenyl phenyl ether and toluene in trifluoroacetic acid or in acetic–sulfuric acid mixtures under nitric oxide

Author(s):  
John H. Atherton ◽  
Roy B. Moodie ◽  
Darren R. Noble ◽  
Brian O'Sullivan
2020 ◽  
Vol 47 (2) ◽  
Author(s):  
Yiqun Lu ◽  
Ling Liu ◽  
An Ning ◽  
Gan Yang ◽  
Yiliang Liu ◽  
...  

2019 ◽  
Vol 23 (04n05) ◽  
pp. 427-436 ◽  
Author(s):  
Lucia Kociscakova ◽  
Merve Ipek Senipek ◽  
Petr Zimcik ◽  
Veronika Novakova

Non-peripherally substituted metal-free and zinc phthalocyanines (Pcs) bearing four diethylamino groups and four Br atoms were prepared. Optimal conditions for synthesis of corresponding precursor ([Formula: see text] 3-bromo-6-(diethylamino)phthalonitrile) either by nucleophilic substitution or by Buchwald–Hartwig coupling were studied. Noteworthy, 3,6-bis(diethylamino)phthalonitrile was also formed, nevertheless only at low yield (typically below 1%) and all attempts for its cyclotetramerization failed. Q bands of prepared Pcs were strongly red shifted up to the near-IR region (769 and 800 nm in THF for zinc and metal-free Pc, respectively). Unusually large hypsochromic shifts of the Q bands, 130 and 80 nm for metal-free and zinc Pc, respectively, were observed upon treating these Pcs with trifluoroacetic acid, which was attributed to the protonation of non-peripheral amines. Treatment with sulfuric acid led to subsequent protonation on the azomethine nitrogens as well. Photophysical study revealed low fluorescence emission of both derivatives ([Formula: see text] <0.03, in THF) and efficient singlet oxygen production only for zinc Pc ([Formula: see text] 0.77 in THF and 0.60 in DMF).


ChemInform ◽  
1987 ◽  
Vol 18 (51) ◽  
Author(s):  
S. POLIZZI ◽  
A. BENEDETTI ◽  
G. FAGHERAZZI ◽  
C. GOATIN ◽  
R. STROZZI ◽  
...  

1966 ◽  
Vol 44 (2) ◽  
pp. 105-109 ◽  
Author(s):  
Stephen J. Kuhn ◽  
John S. McIntyre

Protonation of N,N-dimethylnitrosoamine has been investigated by dissolving the nitrosoamine in different acids and recording the proton magnetic resonance spectra of these solutions. Concentrated sulfuric acid, sulfuric acid monohydrate, perchloric acid (72%), trifluoroacetic acid, and fluorosulfuric acid have been used in this study. Only in fluorosulfuric acid near 0 °C and lower was a new signal observed for the protonated nitrosoamine molecule. Integration of the peaks has shown that only one proton is captured by the nitrosoamine. The following structure is suggested for the protonated nitrosoamine.[Formula: see text]The n.m.r. spectra of fluorosulfuric acid solutions of N,N-diethylnitrosoamine and N-nitrosopiperidine also show separate signals for the captured proton.The n.m.r. spectrum of an equimolar solution of N,N-dimethylnitrosoamine, N,N-dimethylformamide, and trifluoroacetic acid in 2-nitropropane indicates that N,N-dimethylnitrosoamine is a weaker base.


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