Pschorr Reactions with Sulphonamides derived from N-Benzyl-o-phenylenediamine: A New Route to Phenanthridine, and a New Type of Molecular Rearrangement

1963 ◽  
Vol 16 (3) ◽  
pp. 417 ◽  
Author(s):  
JL Huppatz ◽  
WHF Sasse
Keyword(s):  
Acetic Acid ◽  
Sulphuric Acid ◽  
Sodium Nitrite ◽  
Ring System ◽  
Sulphonic Acid ◽  
Diazonium Salts ◽  
Molecular Rearrangement ◽  
New Type ◽  
Cuprous Ions

The preparation in three steps of N-benzyl-N-benzenesulphonyl-o-phenylenediamine (Va), of N-benzyl-N-p-toluenesulphonyl-o-phenylenediamine (Vb), and of N-benzyl-N-methanesulphonyl-o-phenylenediamine (Vc) from o-nitroaniline is described. The copper-catalysed decomposition of diazonium salts of each of these amines in acetic acid-sulphuric acid has been examined. Compound (Va) gave N-benzyl-2-aminobiphenyl (IXa), 5-benzenesulphonyl-5,6-dihydrophenanthridine (VIa), N- benzyl-2-aminobiphenyl-2'-sulphonic acid sultam (Xa), N-benzenesulphonyl-2-amino-biphenyl (XIIa), and phenanthridine. Compound (Vb) gave N-benzyl-2-amino-4'-methylbiphenyl (IXb), 6-p-toluenesulphonyl-5,6-dihydrophenanth (VIb), a compound C20H17NO2S thought to be N-benzyl-2-amino-5'-methylbiphenyl-2'-sulphonic acid sultam (Xb), N-benzyl-N-p-toluenesulphonylaniline (XIb), N-p- toluenesulphonyl-2-aminobiphenyl (XIIb), and phenanthridine. Compound (Vc) gave 5-methanesulphonyl-5,6-dihydrophenanthri (VIc), N-benzyl-N-methanesulphonylaniline (XIc), N-methanesulphonyl-2-aminobiphenyl (XIIc), and phenanthridine. It has been found that the yields of most of these products depend inter alia on the excess of sodium nitrite present during the diazotization prior to cyclization. It is suggested that this effect is caused by changes in the concentration of cuprous ions present during the cyclization. Heterolytic and homolytic processes may be involved in the formation of the dihydrophenanthridines and sultams. The formation of the biphenyl derivatives (IX) and (XII) is postulated to proceed via the spirane intermediates (XIX) or (XX).�The conversion of the sulphonamides of dihydrophenanthridine (VI) to phenanthridine in c. 70% yield completes new syntheses of this ring system.

ChemInform Abstract: THE BIS(TETRATHIOTUNGSTATO)DIAURATE(2-) ANION, A NEW TYPE OF INORGANIC RING SYSTEM

1978 ◽  
Vol 9 (13) ◽  
Author(s):  
A. MUELLER ◽  
H. DORNFELD ◽  
G. HENKEL ◽  
B. KREBS ◽  
M. P. A. VIEGERS
Keyword(s):  
Ring System ◽  
New Type

HYDROLYSIS OF CELLULOSE ACETATE SULPHATE IN ACETONE

1954 ◽  
Vol 32 (9) ◽  
pp. 815-822 ◽  
Author(s):  
Karl Keirstead ◽  
John Myers
Keyword(s):  
Acetic Acid ◽  
Cellulose Acetate ◽  
Sulphuric Acid ◽  
Potentiometric Titration ◽  
Titration Method ◽  
Acetate Ester ◽  
Hydrolysis Of Cellulose ◽  
Potentiometric Titration Method ◽  
Hydrolysis Of

When cellulose acetate sulphate is dissolved in acetone the hydrolysis of the sulphate ester is rapid compared with that of the acetate ester. In 70% acetone the relative rates are reversed. Hydrolysis of the sulphate ester in acetone is greatly affected by the temperature. At 25 °C. or greater the hydrolysis is complete after 24 hr. A potentiometric titration method has been developed for the estimation of sulphuric acid in the presence of smaller amounts of acetic acid.

New Post Etch Polymer Removal Process for Al-Interconnects and Vias in Tank and Spray Tools Using a New Inorganic Chemistry

2005 ◽  
Vol 103-104 ◽  
pp. 381-384
Author(s):  
Raimund Mellies ◽  
Stefan Kunz ◽  
Franz Nilius ◽  
Dieter Mayer ◽  
Andreas Kühner
Keyword(s):  
Inorganic Chemistry ◽  
Hydrogen Peroxide ◽  
Sulphuric Acid ◽  
Environmentally Friendly ◽  
Removal Process ◽  
Dielectric Layers ◽  
New Type ◽  
Etch Residue

A Post-Etch-Residue (PER) removal process for tank and spray tools has been developed using a new inorganic aqueous based chemistry. The performance of this new type of polymer remover, Inosolv 400 Fotopur®, on process wafers is compared with other inorganic chemistries such as DSP (Dilute Sulphuric acid hydrogen Peroxide) and DSP+, containing traces of HF. Inosolv 400 Fotopur® has improved polymer removal capabilities. Furthermore Inosolv 400 Fotopur® does not show any attack of the metal or dielectric layers and is inorganic based and thus environmentally friendly.

Pyrimidine Derivatives and Related Compounds, V Synthesis of Some Isoxazolo [2,3-a] pyrimidines. A New Ring System

1977 ◽  
Vol 32 (3) ◽  
pp. 311-314 ◽  
Author(s):  
Mohamed Hilmy Elnagdi ◽  
Ezzat Mohamed Kandeel ◽  
Kamal Usef Sadek
Keyword(s):  
Acetic Acid ◽  
Hydrochloric Acid ◽  
Ethyl Acetoacetate ◽  
Pyrimidine Derivative ◽  
Ring System ◽  
The Other ◽  
Acid Mixture ◽  
Pyrimidine Derivatives ◽  
Benzoyl Isothiocyanates ◽  
Related Compounds

3-Amino-5-phenyl-4-phenylazoisoxazole (1) reacts with ethyl acetoacetate to yield the corresponding ethyl isoxazolylaminocrotonate derivative (2) which could be thermally cyclized into the isoxazolopyrimidine derivative (4). On the other hand, condensation of 1 with ethoxymethylenemalononitrile has resulted in the formation of the aminoethylene derivative (5).Compound 1 reacted with acrylonitrile to yield the isoxazolo[2,3-a]pyrimidine derivative (6). The latter was converted into the corresponding exo derivative (8) by the action of acetic acid-hydrochloric acid mixture.Compound 1 also reacted with methoxycarbonyl-, ethoxycarbomyl- and benzoyl isothiocyanates to yield the isoxazolylthioureas (10a, b) and (11), respectively. The reaction of 2 with acetic acid-hydrochloric acid and with phenylhydrazine is reported.

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