Abstract
4-Hydroxy-2H-1-benzopyran-2-one
(4) reacts with 1,4-naphthoquinone, 2- methoxy-1,4-benzoquinone and
1,4-benzoquinone in aqueous acetic acid solutions to yield the quinone (6) and
the quinols (11)and (2), respectively. With 5,5-dimethylcyclohexane-1,3-dione,
1,4- naphthoquinone forms a bisfurano compound (9)
while 1,4-benzoquinone yields the bisfurano compound (18) and the monophenolic furano
derivative (17). The blue product formed by acid catalysed dimerization of
2-methoxy-1,4-benzoquinone forms a diacetate, the n.m.r. spectra of which is in
accord with structure (15b).
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