Subject benzoic acid derivatives

The expedient and regioselective metalation of unprotected biphenyl-2-, -3-, and -4-carboxylic acids has been reported.59 Unprotected biphenyl-2-carboxylic acid has been cleanly metalated with. sex-butyllithium at the position adjacent to the carboxylate and can then be subjected to site-selective electrophilic substitution (Scheme 8). The remote C(2 )-position has been attacked by the superbasic mixture of n-BuLi and t-BuOK (LICKOR) in THF or benzene. The resulting dianion cyclizes to give the fluorenone skeleton. The mechanism of the metalation of homologous compounds, 2-(pyridin-3-yl)benzoic acid derivatives, with strong bases has also been discussed.60... 

The function and mechanism of action of peroxides have been the subject of a recent review. The peroxidase activity of ferrihaems continues to be investigated. Deuterioferrihaem peroxide compounds (dpc) formed by reaction of H Og, Bu OOH, and ten peroxybenzoic acids have been characterized. The formation of the dpc from the benzoic acid derivatives is instantaneous. The oxidation of iodide by dpc has been studied using stopped-flow methods, the reactions being first-order with respect to each reactant (kg = 1.6x 10 lmol s ) for all hydroperoxide used at pH >7.75. This result supports the concept that all deuterioferrihaem peroxide compounds are the same oxidized form of deuteriohaem, independent of the nature of the oxidant progenitor. 

The coupling of 2-iodobenzoic acid and phenylacetylene under Sonogashira coupling conditions was found to give a mixture of an isocoumarin derivative and a phthalide (4.40.), The proper choice of the catalyst system led to the preferential formation of the latter compound.53 The process might also be diverted towards the formation of the isocoumarin derivative by isolation of the intermediate o-cthynyl-benzoic acid and its subjection to carefully selected cyclization conditions54... 

Methyl anthraquinone has been obtained by the oxidation of /3-methyl anthracene by several investigators 1 and material of the same origin, obtained by the benzene-extraction of crude commercial anthraquinone,2 has been fully described. As regards the synthesis from phthalic anhydride and toluene, both the preparation and properties of />-toluyl-o-benzoic acid 3 and the complete synthesis 4 have been the subject of several papers. This acid has also been prepared from o-carbomethoxy benzoyl chloride and toluene.5 The phthalic anhydride synthesis of anthraquinone derivatives in general has received considerable attention. An account of this work, together with extensive references, is given by Barnett.6... 

The ozonolysis of diarylfuroxans was studied by Kinney and Harwood. In their earlier paper,272 they found that benzoic acid was formed from diphenylfuroxan, and they interpreted this as evidence for the presence of a C=C bond in the heterocyclic ring, as in structure 4. Later, the isolation of isomeric anisylphenylfuroxans by Meisenheimer et al.22 came to their attention, and Kinney269 subjected the two forms to ozonolysis. Both formed a yellow ozone adduct of unknown composition, which with cold dilute sodium hydroxide gave the salt of the acid derived from the 3-substituent, together with a red residue which on further hydrolysis with hot hydroxide formed the acid of the 4-substituent (Eq. 10). This work provided valuable support for Meisenheimer s contention that his compounds were positional isomers, both based on the furoxan ring structure (1). 

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