The synthesis of benzo[<i>c</i>] cinnoline dioxides

Kempter, Fritz E.; Castle, Raymond N.

doi:10.1002/jhet.5570050428

Cited by 6 publications

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“…In particular, the cyclic structures dissociate much less easily, partly because the associated entropy of dissociation is greatly reduced and the preferred orthogonal trajectory is not easily accessible; in addition, the azodioxy unit is incorporated within an aromatic ring in benzo[ c ]cinnoline-5,6-dioxide and related cyclic structures . Although numerous studies have reported cyclic azodioxides, few have probed the special nature of the cis -azodioxy unit in cyclic compounds. − However, a crystallographic study of the structure of 1,10-dimethylbenzo[ c ]cinnoline-5,6-dioxide ( 12 ), published by Whittleton and Dunitz, reveals that the cis -azodioxy unit is strongly resilient (Figure ). In this structure, significant nonplanarity of the fused aromatic rings is tolerated to minimize steric repulsion of the methyl groups.…”

Section: Aromatic Dinitroso and Polynitroso Compoundsmentioning

confidence: 99%

Dimerization of Aromatic C-Nitroso Compounds

2016

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Aromatic C-nitroso compounds (Ar-N═O) and related species have a rich chemical history, and they continue to interest researchers in many fields. Among the most distinctive and puzzling properties of these compounds is their ability to dimerize reversibly to form azodioxy compounds. The present review subjects this intriguing phenomenon to comprehensive analysis. All aspects of the subject are examined in detail, including the structures of monomeric and dimeric forms, the mechanism of dimerization, features that favor or disfavor dimerization, thermodynamic and kinetic factors, dimerization under specific conditions (including in solution, in the solid state, and on surfaces), and the special associative behavior of dinitroso and polynitroso compounds. By summarizing the current state of knowledge, the review promises to spur further advances in the evergreen field of C-nitroso chemistry, including the discovery of new ways to exploit the reversible dimerization of nitrosoarenes.

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Section: Aromatic Dinitroso and Polynitroso Compoundsmentioning

confidence: 99%

Dimerization of Aromatic C-Nitroso Compounds

2016

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The synthesis of benzo[c]cinnoline 5,6‐dioxides and related compounds

Kempter

Castle

1969

Journal of Heterocyclic Chem

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The preparation of a variety of benzo[c]cinnolines as well as benzo[c]cinnoline monoxides and dioxides by reduction of the corresponding 2,2‐dinitrobiphenyls with hydrogen and Raney nickel of low activity is described. The detailed procedures developed produce superior yields of benzo[c]cinnoline monoxides and dioxides. The structure of some intensely‐colored red‐violet amino, alkylamino, and hydroxybenzo[c]cinnoline monoxides and dioxides is discussed and these are compared with the essentially colorless alkoxyl and acetylamino derivatives. The long wave length band in the U. V. spectrum of the colored compounds is compared.

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An Overview of Synthetic Methods for Preparation of Nitrosoaromatic Compounds

Vančik

2013

Aromatic C-Nitroso Compounds

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The synthesis of benzo[c] cinnoline dioxides

Cited by 6 publications

References 6 publications

Dimerization of Aromatic C-Nitroso Compounds

Dimerization of Aromatic C-Nitroso Compounds

The synthesis of benzo[c]cinnoline 5,6‐dioxides and related compounds

An Overview of Synthetic Methods for Preparation of Nitrosoaromatic Compounds

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