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Interactions of indole derivatives with organic acceptors. III

Wechselwirkungen von Indol-Derivaten mit organischen Akzeptoren, 3. Mitt.

  • Organische Chemie Und Biochemie
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Monatshefte für Chemie / Chemical Monthly Aims and scope Submit manuscript

Abstract

Interactions of 1-hydroxy-2-phenylindole and 2,2′-diphenyl-Δ3,3′-bi-3H-indole with common organic acceptors are analyzed. Depending on the nature of donor-acceptor partners, the reaction may afford molecular complexes, redox products or some kind of adduct. The reaction of 1-hydroxy-2-phenylindole with tetracyanoethylene leads to the formation of 1-oxy-2-phenyl-3-(dicyanomethylidene) indole whose crystal structure is reported.

Zusammenfassung

Es werden die Wechselwirkungen von 1-Hydroxy-2-phenylindol und 2,2′-Diphenyl-Δ3,3′-bi-3H-indol mit organischen Akzeptoren geprüft. Je nach den Eigenschaften des Akzeptors und des Donors kann die Reaktion molekulare Komplexe, Redox-Produkte oder andere Addukte ergeben. Die Reaktion von 1-Hydroxy-2-phenylindol mit Tetracyanoethylen bildet 1-Oxy-2-phenyl-3-(dicyanomethylidene)indol, dessen Kristallstruktur beschrieben wird.

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References

  1. Szent Györgyi A, Isenberg I, Metaglin J (1961) Proc Natl Acad Sci USA 47: 1089

    Google Scholar 

  2. Foster R, Hanson P (1965) Tetrahedron 21: 255

    Google Scholar 

  3. Sung MT, Parker JA (1972) Proc Natl Acad Sci USA 69: 1196

    Google Scholar 

  4. Foster R, Fyfe CA (1966) J Chem Soc B: 926

    Google Scholar 

  5. Cipiciani A, Sartini S, Savelli G (1979) J Chem Soc Faraday I: 497

    Google Scholar 

  6. Foster R, Hanson P (1964) J Chem Soc Faraday II 60: 2189

    Google Scholar 

  7. Sabourault B, Bourdais J (1972) CR Acad Sci Paris 274: 813

    Google Scholar 

  8. Colonna M, Bruni P (1969) Gazz Chim Ital 99: 885

    Google Scholar 

  9. Tosi G, Battistoni P, Bruni P, Cardellini L, Bocelli G (1983) Gazz Chim Ital 113: 153

    Google Scholar 

  10. Freuman F (1980) Chem Rev 80: 329

    Google Scholar 

  11. Fatiadi AJ (1983) Preparation and systhetic applications of cyano compounds. In:Patai S (ed) The chemistry of triple bonded groups. Suppl C. Wiley, p 1057

  12. Colonna M, Bruni P (1967) Gazz Chim Ital 97: 1569

    Google Scholar 

  13. Hindawey AM, Nassar AMG, Issa RM (1977) Acta Acad Sci Hungaricae 92 (3): 263

    Google Scholar 

  14. Issa RM, Abel-Ghani NT, El-Ansary AL, Shoukry AF (1981) Rev Roumanie Chim 26: 667

    Google Scholar 

  15. Issa RM, El-Essawey MM (1973) J Phys Chem (Leipzig) 253: 96;Knoss RD, Fassel VA (1960) J Am Chem Soc 79: 316

    Google Scholar 

  16. Spatz AM, Shackle DR (1976) Tappi 59: 128

    Google Scholar 

  17. Foster R (1979) Molecular association, vol 2. Academic Press, London

    Google Scholar 

  18. Colonna M, Monti A (1962) Gazz Chim Ital 92: 1401

    Google Scholar 

  19. Vogel AI (1957) A textbook of practical organic chemistry, 3rd edn. Longmans, London

    Google Scholar 

  20. Lehmann HS, Larsen FK (1974) Acta Cryst A 30: 580

    Google Scholar 

  21. Belletti D,Ugozzoli F,Cantoni A,Pasquinelli G (1979) Gestione on line di diffrattometro a cristallo singolo Siemens AED con sistema general automation Jumbo 220. Centro di Studio per la Strutturistica Diffrattometrica del CNR, Parma. Internal Reports 1–3/79

  22. Sheldrick GM, SHELX (1976) Program for crystal structure determination. Univ of Cambridge, England

    Google Scholar 

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Authors and Affiliations

  1. Dipartimento di Scienze dei Materiali e della Terra, Facoltà di Ingegneria, Università degli Studi di Ancona, I-60130, Ancona, Italy

    Giorgio Tosi, Liberato Cardellini & Barbara Cardillo

  2. Centro di Studio C.N.R. per la Strutturistica Diffrattometrica, Università di Parma, I-43100, Parma, Italy

    Gabriele Bocelli

Authors
  1. Giorgio Tosi
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  2. Liberato Cardellini
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  3. Barbara Cardillo
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  4. Gabriele Bocelli
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Additional information

Reference [9] is considered part I while part II is in press in Gazz. Chim. Ital.

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Tosi, G., Cardellini, L., Cardillo, B. et al. Interactions of indole derivatives with organic acceptors. III. Monatsh Chem 118, 369–379 (1987). https://doi.org/10.1007/BF00809948

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  • DOI: https://doi.org/10.1007/BF00809948

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