Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Chloromethylation of Dibenzoanthronyls
Syo NAKAZAWA
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1962 Volume 20 Issue 10 Pages 930-935

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Abstract
4, 4'- and 3, 3'-Dibenzoanthronyls were chloromethylated by use of concentrated sulfuric acid and sym-dichlorodimethyl ether to obtain each of their bis-chloro methylated compound, respectively. These dibenzoanthronyls and their chloro methylated compounds were oxidatively decomposed with chromic acid and several kinds of decomposition product were obtained depending on the extent of oxidation. By studying the structure of these compounds, it was confirmed that the chloromethyl group enters into 9, 9'-position. Syntheses of pyridinium salt and isothiuronium salt were made to give watersoluble dyes and their cyclization gave benzoanthrone type vat dyes. Their properties, especially of their dyeing qualities, have been clarified.
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© The Society of Syhthetic Organic Chemistry, Japan
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