9,10-Dihydroanthracene → Anthracene

Participants

Reaction Conditions

Reaction Steps

A solution of 9,10-dihydroanthracene (35 mg; 0.192 mmol) dissolved in 1 mL dry acetonitrile was reacted with tetracyano-1,4-benzoquinone (40 mg; 0.192 mmol) also dissolved in 1 mL dry acetonitrile. After reducing the volume in half and cooling to -20° C. crystals precipitated and were collected. The infrared spectra of the precipitate was identical to that obtained from a mixture of authentic anthracene and tetracyano-1,4-hydroquinone (ν(C≡N)=2239 and 2263 cm-1) verifying that tetracyano-1,4-benzoquinone dehydrogenates 9,10-dihydroanthracene.

Provenance & Evidence