Naphthaldehydeの光酸化反応

概要

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Potential sweep method applied on 1-naphthaldehyde and 2-naphthaldehyde suggested formation of intermediate carbon radicals with elimination of hydrogen from the aldehyde bonded to the 1-position and 2-position, respectively, of the naphthalene ring. Measuemtent, however, was not feasible because of the extreme brevity of life-time of the carbon radicals formed in the course of the electrolytic oxidation but the observed carbon cation pointed to the difference existing between the Ep of 1-naphthalene and that of of 2-naphthalene. Photochemical reaction was introduced to elucidate the behavior of naphthaldehyde, and confirmation of the carbon radicals was made by electron spin resonance (ESR) spectroscopy. To further probe into the oxidation mechanism of naphthaldehyde in the photooxidation reaction, its mixture with hydrogen peroxide was exposed to ultraviolet ray, and while the ESR spectra were examination for carlbon radical behavior, the oxidation was examined with reference to their infrared spectra. The results suggested the following to be the most probable oxidation reaction mechanism for 1-naphthaldehyde and 2-naphthaldehyde.[chemical formula]
公益社団法人日本薬学会の論文
1973-07-25