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Mechanistic studies on the electrohydrodimerization of benzylidenemalononitriles

Untersuchungen zum Mechanismus der Electrohydrodimerisierung von Benzylidenmalonnitril

  • Anorganische Und Physikalische Chemie
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Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Rate constants and activation parameters for the reductive dimerization of substituted benzylidenemalononitriles were obtained from derivate cyclic voltammetry measurements in dimethylformamide as solvent. Benzylidene-,p-methyl-andp-methoxybenzylidenemalononitrile react exclusively via dimerization of their anion radicals (radical-radical coupling) while forp-fluorobenzylidenemalononitrile 25% of the dimerization proceeds by coupling of the anion radical with the substrate.

Zusammenfassung

Mittels derivativer cyclischer Voltammetrie wurden für die Titelreaktion Geschwindigkeitskonstanten und Aktivierungsparameter erhalten (Dimethylformamid als Lösungsmittel). Benzyliden-,p-Methyl- undp-Methoxybenzylidenmalonnitril reagieren ausschließlich über die Dimerisierung ihrer Anionenradikale (Radikal-Radikal-Kopplung), währenddessen die Dimerisierung vonp-Fluorbenzylidenmalonnitril zu 25% über die Kopplung des Anionenradikals mit dem Substrat erfolgt.

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Authors and Affiliations

  1. Laboratory for Organic Chemistry, Norwegian Institute of Technology (NTH), N-7034, Trondheim, Norway

    Olav Lerflaten & Vernon D. Parker

  2. Institut für Organische Chemie und Biochemie, Universität Hamburg, D-2000, Hamburg 13, Federal Republic of Germany

    Paul Margaretha

Authors
  1. Olav Lerflaten
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  2. Vernon D. Parker
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  3. Paul Margaretha
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Additional information

Dedicated to ProfessorO. E. Polansky on the occasion of his 65th birthday.

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Lerflaten, O., Parker, V.D. & Margaretha, P. Mechanistic studies on the electrohydrodimerization of benzylidenemalononitriles. Monatsh Chem 115, 697–704 (1984). https://doi.org/10.1007/BF01120964

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  • DOI: https://doi.org/10.1007/BF01120964

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