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The structural proof of trismethylene-trinitrobenzene: Nucleophilic aromatic addition III

✍ Scribed by Th. J. de Boer; J. C. van Velzen

Publisher
Elsevier Science
Year
2010
Tongue
English
Weight
580 KB
Volume
79
Category
Article
ISSN
0165-0513

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✦ Synopsis

Abstract

“Trismethylene‐trinitrobenzene” has structure IV and not VI (chart 1) as shown by ozonolysis, yielding an aldehydic acid VIII, a dicarboxylic acid IX and, on decarboxylation, a __mono__carboxylic acid X (chart 2). Ozonolysis in methanol leads to products which are consistent with the mechanism put forward by Criegee (chart 3). Oxidation of “trismethylene‐trinitrobenzene” with chromium trioxide results in a ketone XVIII, which can be cleaved by alkali into a carboxylic acid XIX (chart 4), the structure of which is again explicable only with structure IV for the parent compound.

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