Abstract
On the Reaction of Chloranil with Cyanide Ions – an ESR StudyThe reaction of chloranil 1 with cyanide ions in acetonitrile and methanol solutions has been studied. The ESR Spectra revealed the formation of semiquinone anion radicals 7,8, and 9. The latter has been found as its protonated form in methanol only. In addition, both 1 and 2,3‐dicyano‐5,6‐dichloro‐1,4‐benzoquinone 4 gave tetracyanoethylene anion radicals 6 upon reaction with cyanide ions in acetonitrile. Using 13C‐labelled cyanide 6 was shown to originate from the fragmentation of the cyanide addition product to 4. Using the spin trapping technique it was found that no cyanyl free radicals are formed during the thermal reaction of either 1 or 4 with cyanide ions.
Published Version
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