HYPERVALENT IODINE-INDUCED NUCLEOPHILIC-SUBSTITUTION OF PARASUBSTITUTED PHENOL ETHERS - GENERATION OF CATION RADICALS AS REACTIVE INTERMEDIATES
HYPERVALENT IODINE-INDUCED NUCLEOPHILIC-SUBSTITUTION OF PARASUBSTITUTED PHENOL ETHERS - GENERATION OF CATION RADICALS AS REACTIVE INTERMEDIATES
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DOI：
10.1021/ja00088a003
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发表时间：
1994-05-04
影响因子：
15
通讯作者：
OKA, S
中科院分区：
文献类型：
--
作者：
KITA, Y;TOHMA, H;OKA, S
描述了一种新的高价碘在多种亲核试剂的存在下诱导对取代酚醚的亲核取代。紫外和ESR光谱研究表明，该反应是通过阳离子自由基进行的。+]，是由苯酚醚与苯基吡啶（III）双（三氟乙酸酯）（PIFA）的电荷转移（dT）配合物产生的单电子转移（SET）反应中间体。这是第一个涉及芳香族化合物高价碘氧化的自由基中间体的案例。
A novel hypervalent iodine induced nucleophilic substitution of para-substituted phenol ethers in the presence of a variety of nucleophiles is described. UV and ESR spectroscopic studies indicate that this reaction proceeds via cation radicals, [ArH.+], as reactive intermediates generated by single-electron transfer (SET) from a charge-transfer (dT) complex of phenol ethers with phenyliodine(III) bis(trifluoroacetate) (PIFA). This is the first case that involves a radical intermediate on hypervalent iodine oxidations of aromatic compounds.