Novel reactions of 1,2-disubstituted benzenes coordinated to cobalt(III): Neighboring-group participation

Robert J. Balahura, William L. Purcell

Research output: Contribution to journalArticle

29 Citations (Scopus)

Abstract

The pentaamminecobalt(III) complex of 1,2-dicyanobenzene reacts with a stoichiometric amount of base to give the coordinated carboxamido complex (NH3)5Co(2-carboxamidobenzonitrile)2+. The latter complex cyclizes in base to the pentaamminecobalt(III) complex of 1-oxo-3-iminoisoindolin-2-yl. However, in acid solution the coordinated amide complex undergoes an intramolecular rearrangement to form the coordinated nitrile-free amide compound (NH3)5Co(2-cyanobenzamide)3+. This nitrile complex is rapidly hydrolyzed, the reaction involving intramolecular catalysis by the free amide group. The product of the hydrolysis reaction, (NH3)5Co(2-carboxamidobenzamide)2+, cyclizes in acidic solution to (NH3)5Co(1-oxo-3-iminoisoindoline)3+ where the metal is coordinated to the exocyclic nitrogen (3 position). The characterization of the above complexes is described, and mechanisms for their formation are considered.

Original languageEnglish
Pages (from-to)937-941
Number of pages5
JournalInorganic Chemistry
Volume18
Issue number4
StatePublished - Dec 1 1979

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Cobalt
Benzene
Amides
amides
Nitriles
1,2-benzenedicarbonitrile
cobalt
nitriles
benzene
Catalysis
catalysis
hydrolysis
Hydrolysis
Nitrogen
Metals
nitrogen
acids
Acids
products
metals

ASJC Scopus subject areas

  • Inorganic Chemistry

Cite this

Novel reactions of 1,2-disubstituted benzenes coordinated to cobalt(III) : Neighboring-group participation. / Balahura, Robert J.; Purcell, William L.

In: Inorganic Chemistry, Vol. 18, No. 4, 01.12.1979, p. 937-941.

Research output: Contribution to journalArticle

Balahura, Robert J. ; Purcell, William L. / Novel reactions of 1,2-disubstituted benzenes coordinated to cobalt(III) : Neighboring-group participation. In: Inorganic Chemistry. 1979 ; Vol. 18, No. 4. pp. 937-941.
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