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Paper | Regular issue | Vol 32, No. 9, 1991, pp.1709-1717
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5440
Proximity Effect in the Hydrogen-Deuterium Exchange and Deethoxycarbonylation of Peri-substituted Naphthalene with the 1,2,3-Triazole Ring

Yoshinobu Nagawa,* Koichi Honda, and Hiroshi Nakanishi

*National IChemical Laboratory for Industry, 1-1, Higashi, Tsukuba, Ibaraki, 305-8566, Japan

Abstract

The H-D exchange reaction and the deethoxycarboxylation in D2O of 1-[8-(4-ethoxycarbonyl-1H-1,2,3-triazol-1-yl)-1-naphthyl]-3-methyl-4-ethoxycarbonyl-1H-1,2,3-triazolium salts (1) were studied by 1H nmr spectroscopy and compared with those of 1-(1-naphthyl)-3-methyl-4-ethoxycarbonyl-1H-1,2,3-triazolium salts (2). The reaction rates of 1 are found to be much faster than those of 2. The results suggest that the triazole ring in 1 interacts sterically with the N-methylated triazole ring to accelerate the reactions.