Catechol derivatives, 3-halogenated

Pseudomonas putida has been grown with toluene as the sole source of carbon and was found to oxidize chloro-, bromo-, iodo-, and fluorobenzenes to their respective 3-halogenated catechol derivatives (Gibson et al., 1968). The dihydroxy compounds... 

Holmes and his coworkers described a number of pentacoordinated anionic germanium complexes containing a spirocyclic framework with methyl, phenyl, halogen or hydroxyl ligand at the acyclic site307,332,333. Reaction of an organogermanium trichloride with a catechol or thiocatechol derivative in the presence of triethylamine, followed by a metathetical exchange, led to desired products as illustrated by the formation of the phenyl-substituted derivatives 90 and 91 (equation 16)333. 

Derivatives of phenol or aniline can be oxidized to quinones, the yield and ease of oxidation depending on the substituents. If an amino or hydroxyl group is in the para position, the reaction proceeds readily, as illustrated by the synthesis of quinone from hydroquinone by oxidation with a sodium chlorate-vanadium pentoxide mixture (5>6%) or with chromic-sulfuric acid mixture (92%). A para halogen atom usually has a favorable effect. Any group in the para position is eliminated or oxidized. o-Quinones are usually prepared from the corresponding catechols. A survey of procedures for the synthesis of benzoquinones by oxidation has been made. ... 

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