The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Catalytic hydrogenation of coumarone》. Authors are Shuikin, N. I.; Dmitriev, I. I.; Dobrynina, T. P..The article about the compound:5-Iodo-2-furaldehydecas:2689-65-8,SMILESS:IC1=CC=C(O1)C=O).Related Products of 2689-65-8. Through the article, more information about this compound (cas:2689-65-8) is conveyed.
Hydrogenation of coumarone (I) was carried on by the method and with the catalysts previously described (C. A. 33, 1316.1-2). Under all the conditions used the reaction is accompanied by partial cleavage of the furan ring and the formation of 2-ethylcyclohexanol (II) and β-cyclohexylethyl alc. (III). Passing I with H over Pd deposited on asbestos at 175° formed up to 80% octahydrocoumarone (IV), II and some III. In a similar reaction with the Ni catalyst the yield of II was increased to about 50% and that of IV reduced to 21-2%. The liquid-phase hydrogenation of I in EtOH at 20-50° and atm. pressure in the presence of Pt black and platinized charcoal proceeds analogously, but with the intermediate formation of coumaran (2,3-dihydrobenzofuran). IV, b750 170-2°, d420 0.9636, nD20 1.4683, M. R. 36.4. II, b756 182-4°, d420 0.9214, nD20 1.4631, M. R. 38.31. III, b756 203-6°, d420 0.9162, nD20 1.4643.
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Reference:
1,8-Naphthyridine – Wikipedia,
1,8-Naphthyridine | C8H6N2 – PubChem