Journal of Organic Chemistry p. 1814 - 1817 (1981)
Update date:2022-08-28
Topics:
Crouse, David J.
Wheeler, Margaret M.
Goemann, Marti
Tobin, Paul S.
Basu, Swapan K.
Wheeler, Desmond M. S.
Thallium trinitrate (TTN) oxidizes 1,5-naphthalenediol (1a) and its monomethyl ether (1b) in good yield to juglone (2a) and its methyl ether (2b), respectively.Oxidation of 1b with TTN in a mixture of ethylene glycol and trimethyl orthoformate gave 2c (the 4-monoacetal of 2b), which is a promising intermediate in the synthesis of daunomycinone (3a) and some of its analogues.This is the first direct oxidation of a para-unsubstituted phenol to a monoacetal of a quinone.
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