Silver(I) oxide mediated highly selective monotosylation of symmetrical diols.: Application to the synthesis of polysubstituted cyclic ethers
Silver(I) oxide mediated highly selective monotosylation of symmetrical diols.: Application to the synthesis of polysubstituted cyclic ethers
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DOI：
10.1021/ol020071y
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发表时间：
2002-07-11
期刊：
影响因子：
5.2
通讯作者：
Sauvé, G
中科院分区：
文献类型：
--
作者：
Bouzide, A;Sauvé, G
对称二醇和低聚（乙二醇）与化学计量量的对甲苯磺酰氯在银（I）氧化物和催化量的碘化钾存在下的反应以高产率选择性地产生单甲苯磺酸酯衍生物。用过量的银氧化物处理相应的二醇，容易得到多取代的环醚。高选择性的基础上解释的两个羟基之间的酸性差异，这经历了分子内氢键。
[GRAPHICS]The reaction of symmetrical diols and oligo(ethylene glycol)s with a stoichiometric amount of p-toluenesulfonyl chloride in the presence of silver(l) oxide and a catalytic amount of potassium iodide led selectively to the monotosylate derivatives in high yields. Polysubstituted cyclic ethers were obtained readily upon treatment of the corresponding diols with an excess of silver oxide. The high selectivity was explained on the basis of the difference in acidity between the two hydroxy groups, which undergo an intramolecular hydrogen bonding.