Hydroxylation of Nitrated Naphthalenes with KO2/Crown Ether.
作者:Kiyoshi FUKUHARA、Yukie HARA、Ikuo NAKANISHI、Naoki MIYATA
DOI:10.1248/cpb.48.1532
日期:——
Superoxide radical anion (O·-2), generated by KO2/crown ether, is effective for hydroxylation of nitronaphthalenes. When mono- and di-nitronaphthalenes are treated with KO2/crown ehter, hydroxylation results at the electron-deficient site caused by the electron withdrawing effect of the substituted nitro group. Kinetic experiments suggest that the hydroxylation proceeds by two different mechanisms dependent on the first one-electron reduction potential of nitronaphthalenes.
由 KO2/冠醚生成的超氧自由基阴离子(O--2)可有效地对硝基萘进行羟基化。当用 KO2/冠醚处理一硝基和二硝基萘时,由于取代的硝基的退电子效应,在缺电子位点发生羟基化反应。动力学实验表明,羟基化作用有两种不同的机制,取决于硝基萘的第一单电子还原电位。