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- Title
Über 3,3,6,9,9-Pentamethyl-2,10-diaza-bicyclo-[4.4.0]-1-decen und einige seiner Derivate. Über synthetische Methoden. 13. Mitteilung.
- Authors
Heinzer, Franz; Soukup, Milan; Eschenmoser, Albert
- Abstract
3,3,6,9,9-Pentamethyl-2,10-diaza-bicyclo[4.4.0]-1-decen and some of its derivatives A simple synthesis for the bicyclic amidine 1 ( Scheme 3) is described. This base and the salts which were prepared from it show solubility characteristics which make the amidine a potentially useful reagent for salt formation of carboxylic acids and related proton complexes of bidentate ligands. Among the derivatives made from 1 are the sterically strongly hindered N-alkylated amidines 11, 12 and 14 ( Scheme 5), as well as the stable crystalline N1-oxidoamidine- N2-oxyl radical 2 ( Scheme 6). The ability of the latter to serve as a paramagnetic chelating ligand for metal ions is illustrated by the preparation of a corresponding nickel(II) complex. The radical is also a source for the α-nitronyl-nitrosonium cation 4 which shows in its reactivity towards conjugated dienes and olefines some of the expected resemblance to singlet oxygen.
- Publication
Helvetica Chimica Acta, 1978, Vol 61, Issue 8, p2851
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19780610812