First examples of arylazo derivatives of
cyclooctatetraene
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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