Anthrahydroquinone derivatives

The capability of anthrahydroquinone derivatives to afford corresponding anthraquinones and HjOj in the course of autoxidation, through decomposition of intermediate HP (Eq. 14.9), consti-mtes a basis for the main industrial process of the hydrogen peroxide production (the Riedl-f eiderer process) [22]. 

The peroxyoxalate chemiluminescence is used here, too warning capsules against infiltrating troops were developed containing an active oxalate, a fluorescer, and - as a hydrogen peroxide source, producing H2O2 on contact with air - an anthrahydroquinone derivative (258). 

Ralph, J. Landucci, L. L. Adducts of anthrahydroquinone and anthranol with lignin model quinone methides. 2. Dehydration derivatives. Proof of threo configuration. J. Org. Chem. 1983, 48, 372-376. 

Unfortunately anthrahydroquinone is not very stable under acid conditions, which are needed for a reversible cyclization of the benzoquinone derivatives. There is an early preparative observation on the rapid formation of anthraquinone (AQ) 3 and anthrone (Ant) 4 from anthrahydroquinone (AQH2) 1 in cold concentrated sulfuric acid [83] according the overall reaction... 

The photoinduced reduction of some quinones by zinc porphyrin and also by its tetraphenyl derivative has been studied in micellar systems. The mean time for intramicellar electron transfer has been established as 0.2 ps, and for duroquinone the rates of entry and exit from the micelle have been found to be 5 x 10 m s and6 x 10 m s respectively. Quinones possessing long chains are less mobile and partial charge separation could be achieved. Irradiation of anthraquinone in aqueous sodium dodecyl sulphate leads to anthraquinol and the surfactant-anthrahydroquinone ether as major products via the triplet state of the anthraquinone. ... 

Anthraquinones are the most widespread group of natural quinones. They occur in higher plants, fungi, lichens and some inseds. Anthraquinones are accompanied by derivatives of anthranol, anthrahydroquinone (9-155) and their oxo forms anthrone and oxanthrone (9-156), which are, as glycosides, precursors of anthraquinone pigments. 

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