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- Title
Valenzisomere aromatischer systeme. Die Synthese des Pyrrolo-3-azabenzvalens.
- Authors
Burger, Ulrich; Dreier, Francine
- Abstract
Valence Isomers of Aromatic Systems. The Synthesis of Pyrrolo-3-azabenzvalene 4-Azapentalenyl anion ( 4) is shown to react with dichloromethane/butyl lithium in two fundamentally different ways depending on whether diethyl ether or tetrahydrofuran is chosen as solvent. In the first case a tetracyclic valence isomer of indolizine, i.e. pyrrolo-3-azabenzvalene ( 6) is formed together with indolizine ( 8) itself. In THF however, a pyrrylbutenyne ( 9), isomeric with the products mentioned above is obtained in a stereospecific reaction. Once again the appearance of indolizine ( 8) accompanies the reaction. Mechanistic implications, based on the finding that the heterovalene 6 is not a precursor of the pyrrylbutenyne 9, are discussed.
- Publication
Helvetica Chimica Acta, 1979, Vol 62, Issue 2, p540
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19790620222