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Electron transfer from dibenzo[b,f]-1-azapentalene dianion: Attempted synthesis of dibenzo[b,f]-1-azapentalene

Elektronentransfer von Dibenzo[b,f]-1-azapentalen-Dianion: Ein Versuch zur Synthese von Dibenzo[b,f]-1-azapentalen

  • Organische Chemie Und Biochemie
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Abstract

When dibenzo[b,f]-1-azapentalene dianion (3) was allowed to react with either iron (III) chloride or ethylene bromide, a one-electron transfer from3 took place readily to give the radical anion11. Further electron transfer from11 did not occur presumably due to the antiaromatic character of dibenzo[b,f]-1-azapentalene (1) that would have resulted. The radical anion11 underwent further transformation by hydrogen abstraction from the solvent to give 5,10-dihydroindeno[1,2-b]indole (2) and by dimerization to themeso and (R,S) isomers of 5,5′,10,10′-tetrahydro-10,10′-biindeno[1,2-b]indole (4 a and4 b) respectively.

Zusammenfassung

Die Reaktion von Dibenzo[b,f]-1-azapentalen-Dianion (3) mit Eisen (III) oder Ethylenbromid ergab einen Ein-Elektronentransfer zum Radikalanion11. Ein weiterer Elektronentransfer fand nicht statt, vermutlich wegen des antiaromatischen Charakters von Dibenzo[b,f]-1-azapentalen (1), das dabei entstehen müßte. Das Radikalanion11 ergab unter Wasserstoffentzug aus dem Lösungsmittel 5,10-Dihydroindeno[1,2-b]indol (2), das weiter zummeso- bzw. (R,S)-5,5′,10,10′-tetrahydro-10,10′-biindeno[1,2-b]indol (4 a bzw.4 b) dimerisierte.

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References

  1. Eisch J. J.,Abraham T., Tetrahedron Lett.1972, 953.

  2. Abraham T., Ph.D. Dissertation, The Catholic University of America, Washington, D.C., 1976.

    Google Scholar 

  3. Eisch J. J.,Abraham T., Tetrahedron Lett.1976, 1647.

  4. Abraham T., Curran D., Tetrahedron38, 1019 (1982).

    Google Scholar 

  5. Harvey R. G., Cho H., J. Amer. Chem. Soc.96, 2434 (1974).

    Google Scholar 

  6. Bavin P. M. G., Can. J. Chem.38, 882 (1960).

    Google Scholar 

  7. Bethell D.,Cockerill A. F.,Frankham D. B., J. Chem. Soc. B1967, 1287.

  8. Brugel W., Nuclear Magnetic Resonance Spectra and Chemical Structure, Vol. 1. Academic Press. 1967.

  9. Rabinovitz M.,Agranat I.,Bergmann E. D., Tetrahedron Lett.1965, 1265.

  10. Olah G. A., Field L. D., Watkins M. I., Malhotra R., J. Org. Chem.46, 1761 (1981).

    Google Scholar 

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Authors and Affiliations

  1. Research Institute, University of Dayton, 45469, Dayton, OH, U.S.A.

    Tonson Abraham

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  1. Tonson Abraham
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Abraham, T. Electron transfer from dibenzo[b,f]-1-azapentalene dianion: Attempted synthesis of dibenzo[b,f]-1-azapentalene. Monatsh Chem 113, 1275–1282 (1982). https://doi.org/10.1007/BF00808743

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  • DOI: https://doi.org/10.1007/BF00808743

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