Journal of the Chemical Society. Perkin transactions I p. 493 - 497 (1981)
Update date:2022-08-05
Topics:
Coutts, Ian G. C.
Hamblin, Michael R.
Welsby, Sheila E.
The oxidation with active manganese dioxide of a series of 2,4'-dihydroxydiphenyl ethers to the corresponding p-benzoquinone monoacetals (1,3-benzodioxole-2-spirocyclohexadien-4'-ones) is described; among the dienones prepared were monoacetals of nitro-p-benzoquinone and of p-fluoranil.Attempted ether formation with 2,6-di-t-butyl-4-bromophenol and either 2- or 3-methoxyphenol failed, small quantities of unsymmetric biphenyls being formed in a novel arylation reaction.A spirobenzoxazole can be prepared by oxidation of a 2,4'-dihydroxydiphenylamine.Substituent effects in the hydrolysis of derived spirodienols have been observed.
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