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HERO ID
8109616
Reference Type
Journal Article
Title
Synthesis of anthracene homologues. Part I. 2:6- and 2:7-dimethylanthracenes
Author(s)
Morgan, GT; Coulson, EA
Year
1929
Is Peer Reviewed?
Yes
Journal
Journal of the Chemical Society
ISSN:
0368-1769
Page Numbers
2203-2214
Language
English
DOI
10.1039/jr9290002203
Abstract
(1) 2:7-Dimethylanthracene (m. p. 241° corr.) has been synthesised by a method which establishes definitely the orientation of the two methyl groups, and the hydrocarbon has been oxidised to 2:7-dimethylanthraquinone (m. p. 170° corr.). (2) These 2:7-dimethyl derivatives are identical respectively 4 F 2 with the "A" dimethylanthracene (m. p. 240°) and its quinone (m. p. 169°) isolated by Lavaux and considered to have the 1:6-configuration. This orientation is now shown to be incorrect. (3) 2:6-Dimethylanthracene (m. p. 250° corr.) has been synthesised definitely and oxidised to 2:6-dimethylanthraquinone (m. p. 242° corr.). (4) These 2:6-dimethyl derivatives are identical respectively with "B" dimethylanthracene and its quinone isolated by Lavaux and regarded by him as 2:7-derivatives, although the correct 2:6-orientation was suggested subsequently by Seer. (5) The heavy neutral oils of low-temperature tar from the carbon-isation of bituminous coal contain a mixture of anthracene derivatives from which 2:6- and 2:7-dimethylanthraquinones have been obtained by oxidation.
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