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Azonia polycyclic quinones, o ‐diazo‐oxides and related products
Author(s) -
Fields D. L.,
Miller J. B.
Publication year - 1970
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570070113
Subject(s) - chemistry , diazo , electrophile , anthracene , hydrogen chloride , methanol , nitric acid , chloride , medicinal chemistry , organic chemistry , catalysis
4α‐Azoniaanthracene‐5,6‐ and 5,8‐dione salts have been prepared by nitric acid oxidation of their respective diols, and are shown to function as either an electrophilic dienophile or a diene component in Diels‐Alder‐type reactions. Several azonia o ‐quinones have been treated with tosylhydrazine in methanol saturated with hydrogen chloride to give unusually stable o ‐diazo‐oxides. A four‐step dehydroxylation procedure is detailed for the conversion of .5,6‐dihydroxy‐4α‐azonia‐anthracene salts to new 5‐hydroxy‐4α‐azoniaanthracene salts.