Is anyone of you aware of a general instruction for carrying out a Wohl-Aue-Reaction?
If searched for this for quite a long time, but I haven't found one yet.
Thank you in advance.solo - 15-6-2008 at 07:25
........information of the afore asked reaction, also a study using the reaction......solo
Excerpt
.....Until recently, in addition to the direct oxidation of phenazines, the Wohl--Aue con- densation of nitrobenzenes and anilines in the presence of
bases was practically the only method for the synthesis of phenazine N-oxides. Recently developed preparative methods have facilitated the approach to
known compounds and have made it possible to synthesize new com- pounds. The original method of Haddadin and co-workers 135] is based on a completely
new : principle for the construction of thephenazine ring. The authors have observed that benzo- furoxan (III) reacts with l-morpholinocyclohexene to
give 1,2,3,4-tetrahydrophenazine N,N'- dioxides.
.........as read here,
Recent advances in the chemistry of phenazine oxides (review) S. Pietra1, G. F. Bettinetti1, A. Albini1 and G. Minoli1 Chemistry of Heterocyclic Compounds Volume 13, Number 12 / Pages 1263-1274, December, 1977
Abstract
Data on the electronic structures and spectral characteristics of phenazine 5-oxides and 5, 10-dioxides are correlated. Methods for the synthesis of
N-oxides of the phenazine series and their reactions (reduction, electrophilic and nucleophilic substitution, and photochemical transformations) are
examined. Data on the natural compounds of this series are presented.
Thank you for this, but it isn't exactly what I've been looking for.
This study shows methods to avoid the Wohl-Aue-Reaction, but the latter seems to me to be the only suitable way to sythesize Phenazine, considering my
equipment.solo - 15-6-2008 at 14:44
The Wohl-Aue Reaction. I. Structure of Benzo [a] phenazine Oxides and Syntheses of 1,6-Dimethoxyphenazine and 1,6-Dichlorophenazine Irwin J. Pachter, Milton C. Kloetzel J. Am. Chem. Soc. 1951; 73(10); 4958-4961
Abstract
The Wohl-Aue reaction between nitrobenzene and 2-naphthylamine in the presence of alkali yielded benzo [alphenazine-
Of The This novel 1,6-Dimethoxy- and 1,6-dichlorophenazine were prepared by the Wohl-Aue method in attempts to establish the struc-
12-oxide which was not identical with benzo[a]phenazine-7-oxide derived from the oxidation of benzo [alphenazine.
the two rnonooxides, only the Wohl-Aue compound readily yielded benzo[a]phenazine-7,12-dioxide on oxidation.
dioxide was reduced to the 7-oxide on treatment with a warm solution of hydrogen peroxide in acetic acid.
reduction was not effected by hot acetic acid in the absence of peroxide. ture of, and to conveniently synthesize, the antibiotic pigment iodinin.
Ueber die Einwirkung von Nitrobenzol auf Anilin bei Gegenwart von Alkali A. Wohl, W. Aue Berichte der deutschen chemischen Gesellschaft Volume 34, Issue 2 , Pages 2442 - 2450, 1901
Is anyone of you aware of a general instruction for carrying out a Wohl-Aue-Reaction?
If searched for this for quite a long time, but I haven't found one yet.
Thank you in advance.
I have stated a number of times that starting a thread in the Organic chemistry section requires expresing the question clearly and with references so
that it actually becomes answerable (also for not causing overaltruistic members losing time searching for basic information). Since
you did not bother to provide the minimum background information needed, I'm moving this thread to Beginnings where this type of questions are welcome
and acceptable.ChemoMax1 - 16-6-2008 at 01:57
Thank you very much, solo.
This is exactly what I've searched.
