o-キイノド型過塩素化フェノール類とピリジン塩基との反応

概要

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Among perchlorinated phenols, those of the o-quinonoid type (3, 5-cyclohexadien-one-1) are rich in reactivity (cf. S. Kumamoto, Kogyo Kagaku Zasshi, 64, 181 (1961)). The reaction of 2, 2, 4, 6-tetrachloro-3, 5-dimethyl- (A) and 2, 2, 3, 4, 5, 6-hexachloro-3, 5-cyclohexadienone-1 (B) with pyridine bases were studied and obained the following results. (A) and (B) reacted with pyridine in chloroform solution to yield pyridinium chlorides (AP), (BP) involved 1 mol. water of crystallization respectively, which are easily soluble in water or alcohols. Treating (AP) and (BP) above with 28% NH_4OHaq. or NaOHaq. yellow crystals of pridinium hydroxide, (AP') and (BP') were obtained. And furthermore, it was found that (AP') and (BP') added conc. HCl to return to the original (AP) and (BP) respectively. Through the infrared spectra, these compounds were understood to be 2, 4, 6-trichloro-3, 5-dimethylphenoxy-pyridinium chloride (AP), -pytidinium hydroxide (AP') and 2, 3, 4, 5, 6-pentachloro-phenoxy-pyridinium chloride (BP), -pyridinium hydroxide (BP'). And in the reaction of other pyridine bases (α-, β-, γ-picoline and 2, 6-lutidine)　with (A) and (B), pure compounds were not obtained.
鹿児島大学,カゴシマダイガク,Kagoshima Universityの論文