Scientific article

Valenzisomere aromatischer systeme. Die Synthese des Pyrrolo-3-azabenzvalens

Published inHelvetica chimica acta, vol. 62, no. 2, p. 540-545
Publication date1979-03-07

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.

Citation (ISO format)
BURGER, Ulrich, DREIER, Franziska. Valenzisomere aromatischer systeme. Die Synthese des Pyrrolo-3-azabenzvalens. In: Helvetica chimica acta, 1979, vol. 62, n° 2, p. 540–545. doi: 10.1002/hlca.19790620222
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Article (Published version)
ISSN of the journal0018-019X

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