The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Kolbe electrolyses of cis- and trans-methyl hydrogen hexahydrophthalate》. Authors are Overberger, C. G.; Kabasakalian, Peter.The article about the compound:cis-Cyclohexane-1,2-dicarboxylic acidcas:610-09-3,SMILESS:O=C([C@H]1[C@@H](C(O)=O)CCCC1)O).Application In Synthesis of cis-Cyclohexane-1,2-dicarboxylic acid. Through the article, more information about this compound (cas:610-09-3) is conveyed.
The Kolbe electrolysis of cis- and trans-Me H hexahydrophthalate (I) in anhydrous MeOH has been carried out. Identical mixtures of uncoupled products were obtained from both isomers. Me 1-cyclohexene- and 2-cyclohexene-1-carboxylate and Me cyclohexanecarboxylate were obtained as monomeric products. Dimeric materials were obtained for the first time from I. Saponification of the dimeric ester mixture gave 2 perhydrodiphenic acids, trans-anti-trans and trans-syn-trans, which were separated and identified quantitatively by adsorption chromatography and infrared analysis. Since epimerization occurred on all centers α to the carboxyl group, no conclusion about the stereochemistry of the radicals could be deduced from the ratios of coupled products.
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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics