The 9-methyl-8a,10a-diazoniaphenanthrene cation, an aromatic ring system with two quaternary nitrogen bridgehead atoms in one ring
✍ Scribed by I.C. Calder; W.H.F. Sasse
- Publisher
- Elsevier Science
- Year
- 1964
- Tongue
- French
- Weight
- 166 KB
- Volume
- 5
- Category
- Article
- ISSN
- 0040-4039
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✦ Synopsis
THE first aromatic rzingsystemswith quaternarynitrogenatoms attwobridgehead positions were recently prepared by Bradsher and Perhem (1). These authors describe several isomeric diazoniapentaphene salts, e.g., (I), in which the two quatercarynitm~ atoms arelocated in different rings. Among factors of interest determining the chemistry of ions of this type are the mutual. repulsion between the two positive charges and the extent to which these charges are delocalised. These considerations have prompted us to study the chemistry of tricyclic aromatic compounds inwhich two quaternarynitrogen atoms are situated at bridgehead positions in one ring. We now report the first synthesis of one of these ions, the 9+netbyl4a,lOa-diasoniaphenantbrene cation (II).