SCHEDULED MAINTENANCE:
Anthrone gives Diels-Alder adducts with dimethyl acetylenedicarboxylate and with maleic anhydride, which have been shown to be 9,10-bridged derivatives of 9-anthrol. The adduct with maleic anhydride rearranges on heating to give 10-anthronylsuccinic anhydride. Reaction of some other dienophiles (tetracyanoethylene, diethyl azodicarboxylate, or chloranil) with anthrone gives bianthron-9-yl.
The n.m.r. spectra of these compounds are discussed.
D. Cohen, I. T. Millar and K. E. Richards, J. Chem. Soc. C, 1968, 793 DOI: 10.1039/J39680000793
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