以对氨基苯磺酸为起始原料,通过重氮化、缩合和水解反应,合成了3,5-二甲基-4-羟基苯胺盐酸盐,总收率为75％.用3,5-二甲基-4-羟基苯胺盐酸盐制备了-50℃下稳定的3,5-二甲基-4-羟基苯基五唑,收率为66.7％.以甲醇为溶剂,亚铁盐为还原剂,间氯过氧苯甲酸为氧化剂,可切断3,5-二甲基-4-羟基苯基五唑分子中的C-N键,得到少量的五唑负离子,并通过质谱、核磁等方法对其进行表征.同位素标记实验证明五唑环中N原子具有相同的化学环境,说明五唑负离子极有可能具有芳香性.%3,5-Dimethyl-4-hydroxy aniline hydrochloride was synthesized with a total yield of 75％ from p-aminobenzene sulfonic acid via diazotization,condensation and hydrolysis reaction.3,5-Dimethyl-4-hydroxy phenyl-pentazole,which is stable at-50 ℃was synthesized from 3,5-dimethyl-4-aniline hydrochloride,and the yield was 66.7％.A small amount of pentazole anion was synthesized from 3,5-dimethyl-4-hydroxy phenyl-pentazole by using methanol as solvent,ferrous salts as reductant,and m-chloroperoxybenzoicacid as oxidant to break the C-N bond.Pentazole anion was characterized by MS and NMR.According to the isotope labeling experiments,nitrogen atoms in pentazole anion are in the same chemical environment,which means pentazole anion may possess aromaticity.
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