The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Photochemical transformations. XI. Isomerization of 1,3-cyclooctadiene》. Authors are Dauben, William G.; Cargill, Robert L..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).Electric Literature of C8H12O4. Through the article, more information about this compound (cas:610-09-3) is conveyed.
cf. CA 54, 22718a. Com. 1,3-cyclooctadiene (I, n2D0 1.4940, λ 228 mμ (ε 5470, alc.), 22.1 g.) in 2 l. dry Et2O irradiated 200 hrs. with a Hanovia high pressure Hg arc lamp, internal probe, type L with magnetic stirring (He atm.), the progress of irradiation followed by ultraviolet spectroscopy to disappearance of I, the Et2O evaporated at 40-50° through a 1 ft. Vigreux column, and the yellow residue distilled through a Nester-Faust 2 ft. spinning band column gave 36-41% bicyclo[4.2.0]oct-7-ene (II), C8H12, b. 131-2°, n2D0 1.4720, λ205 mμ (ε 700, alc.), nuclear magnetic resonance singlets at 4.04 and complex multiplets at 7.21, 8.47 τ, infrared spectrum identical with that of material prepared from cyclooctatetraene dibromide. NaIO4 (9.78 millimoles), 0.16 millimole KMnO4, and 0.37 millimole K2CO3 in 200 ml. H2O stirred 25 hrs. at 25° with 1.03 millimoles II, the mixture acidified with 15% H2SO4, extracted 20 hrs. with Et2O, the dried extract evaporated, and the residue triturated with petr. ether gave 105 mg. solid, recrystallized from H2O and from Et2O-petr. ether to give cis-1,2-cyclohexanedicarboxylic acid, m. 197.5-8.0°. At no time was the typical spectrum of 1,3,5-hexatriene detected in the ultraviolet absorption spectrum of the irradiated solution
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Reference:
Benzisoxazole – Wikipedia,
Benzisoxazole – an overview | ScienceDirect Topics