The structural proof of trismethylene‐trinitrobenzene: Nucleophilic aromatic addition III
- 1 January 1960
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 79 (4) , 430-442
- https://doi.org/10.1002/recl.19600790411
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 monocarboxylic 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.Keywords
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