The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Stereochemistry of catalytic hydrogenation. V. The assignment of cis and trans configurations》. Authors are Linstead, R. P.; Davis, Selby B.; Whetstone, Richard R..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).Synthetic Route of C8H12O4. Through the article, more information about this compound (cas:610-09-3) is conveyed.
cis-Hexahydrodiphenic acid (m. 240-1°) (I) with concentrated and fuming HNO3 gives only NO2 products and KMnO4 yields no useful products. I. (1g.) in 20 cc. warm AcOH, treated with O3 for 4 hrs. and then overnight with 50 cc. 3% H2O2 and the material separated by fractional acidification, gives about 0.5 g. unchanged I and 128 mg. (crude) cis-hexahydrophthalic acid (identified as the cis-dianilide, m. 238° and the phenylimide). This establishes the structure of I, of the acid m. 289° as cis-syn-cis-perhydrodiphenic acid and of the acid m. 223° as the trans-syn-trans isomer. trans-Δ10-9-Ketododecahydrophenanthrene (Rapson and Robinson, C. A. 29, 7996.1) with O3 in AcOH gives 2.45 g. of trans-2-keto-1, 1′-bicyclohexyl-2′-carboxylic acid (II), a pale yellow oil, isolated as the oxime (3.07g.), m. 162-3°. On acetylation and subsequent pyrolysis II is converted into an unsaturated lactone (not obtained pure) which is oxidized by KMnO4 to a poor yield of trans-hexahydrophthalic acid, m. 227-9° (after repeated crystallization from H2O; 215-20° given in the literature). This series of reactions is not as unequivocal as the oxidation of I. cis-9-Keto-as-octahydrophenanthrene (III) (cf. part VI) (0.4 g.), heated on the steam bath for 15 min. with 5 cc. concentrated HNO3 and 3 cc. fuming HNO3, gives 20 mg. cis-nitrohexahydrodiphenic acid (IV), m. 217-19°, and 0.1 g. of a tri-NO2 derivative of III, m. 151-2°. Heating 500 mg. of III with 1 cc. concentrated HNO3 and 1 cc. fuming HNO3 gives a di-NO2 derivative of III, m. 152°; this gives the tri-NO2 derivative with HNO3 on the steam bath. trans-III (350 mg.) with HNO3 gives about equal amounts (100 mg.) of trans-IV and the tri-NO2 derivative, needles from AcOH, m. 182-4°, or plates from hexane, m. 182.5-3.5°. The stereochem. implications of these results are discussed and it is shown that they are in agreement with other, less exact, evidence.
As far as I know, this compound(610-09-3)Synthetic Route of C8H12O4 can be applied in many ways, which is helpful for the development of experiments. Therefore many people are doing relevant researches.
Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics