Journal of Organic Chemistry p. 1251 - 1255 (1981)
Update date:2022-08-28
Topics:
Hart, Harold
Nwokogu, Godson
Low-valent forms of iron, tungsten, and titanium, produced by treatment of the metal chlorides with butyllithium at -78 deg C, are useful deoxygenation catalysts for the conversion of 1,4-endoxides to the corresponding arenes in a single step.In some instances, particulary with highly substituted endoxides, other reactions may interefere.For example, with methyl substituents at C2 and C3 and with reduced iron, reduction of the C2-C3 double bond and a 1,3 hydrogen shift occur.Also, hindered aromatic methoxyls may be replaced by hydrogen.Use of this deoxygenationmethod to prepare 1,4,5,8,9,10-hexamethylanthracene, a compound with multiple peri interactions, is described.
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