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DOI: 10.1039/A604933H (Paper) Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 747-750

First examples of arylazo derivatives of cyclooctatetraene[hair space]

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Zori V. Todres and Ghevork Ts. Hovsepyan

Abstract

Disodium and dipotassium derivatives of 1,6-dinitrocyclooctatetraene (substrates) react with benzenediazo compounds (reagents) in THF to yield bis(azo)- or nitro(azo)-cyclooctatetraenes, the first cyclooctatetraene arylazo derivatives. Structures of the azo compounds are established by conventional methods and confirmed by X-ray crystallography. Together with the main products of electrophilic substitution, products of substrate-to-reagent electron transfer are formed. The electron-transfer products predominate with DMSO instead of THF as a solvent. The difference is apparently a result of ion-pair disintegration in the case of the substrate reactions when DMSO, a strong dissociating solvent, is used.

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