Issue 0, 1971
From the journal:

Journal of the Chemical Society C: Organic

On the dealkylation of aromatic ethers with nitrous acid

D. H. R. Barton,   P. G. Gordon  and  D. G. Hewitt  

Abstract

Monoethers of hydroquinone and of catechol, in which the aromatic hydrogen atoms are hindered towards electrophilic substitution by bulky substituents, are smoothly converted into the corresponding quinones and alcohols on treatment with nitrous acid. The mechanism of this reaction has been elucidated with the aid of appropriate 18O-labelled compounds. In certain cases dialkyl ethers are similarly converted into quinones by nitrous acid. The mild conditions needed for these dealkylations makes the method of potential value for compounds with the appropriate substitution pattern.

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Article information

DOI
https://doi.org/10.1039/J39710001206
Article type
Paper

J. Chem. Soc. C, 1971, 1206-1210

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On the dealkylation of aromatic ethers with nitrous acid

D. H. R. Barton, P. G. Gordon and D. G. Hewitt, J. Chem. Soc. C, 1971, 1206 DOI: 10.1039/J39710001206

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