16638
Accession Number
28387
Author
Brunauer, Stephen; Emmett, P.H.; Teller, Edward
Title Of Article Chaper
Adsorption of gases in multimolecular layers
Title Of Journal Book
American Chemical Society. Journal
Volume
60
Pages
309-319
Reference Bibliography
Includes bibliog. refs.
Language Of Text
English
Literature Type
Serial
Literature Level
Analytic
Abstract
In a recent article, Akin, Stamatoff, and Bogert reported the synthesis of 1,4-dimethylphenanthrene from p-xylene by the familiar Pschorr reaction, in which they obtained a product quite different from that secured from the same initial material by Bardhan and Sengupta, by another series of reactions, and to which the latter investigators assigned the same constitution. The experimental results published by Akin, Stamatoff, and Bogert indicated, however, that the Bardhan and Sengupta hydrocarbon was probably the 1, 3-dimethyl isomer, previously prepared by Bogert and Stamatoff, and by Haworth, Mavin, and Sheldrick. At the time, it was suggested by Akin, Stamatoff, and Bogert, although they could not rearrange their own product to the 1,3-dimethyl isomer by selenium diffusion, that perhaps something of this kind had happened in the final step of the Bardhan and Sengupta synthesis. We have therefore synthesized the 1, 4-dimethylphenanthrene by two slightly different methods, from p-xylylethyl cyclohexanols, dehydrogenating the resulting octahydro compounds by either sulfur or selenium, as the final step, and in both cases obtained a dimethylphenanthrene whose properties agreed with the 1,4-compound of Akin, Stamatoff, and Bogert, and without any evidence of the migration of one of the p-xylene methyl groups under the conditions of our experiments. Our suggested explanation of Bardhan and Sengupta's results, therefore, is not supported by this evidence. These two syntheses were as shown in the chart.
pub_id
16638