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使用 Oxone 和三氟乙酸氧化有机碘化物,制备[双(三氟乙酰氧基)碘]全氟烷烃和[双(三氟乙酰氧基)碘]芳烃的通用且方便的方法。

A general and convenient preparation of [bis(trifluoroacetoxy)iodo]perfluoroalkanes and [bis(trifluoroacetoxy)iodo]arenes by oxidation of organic iodides using oxone and trifluoroacetic acid.

机构信息

University of Minnesota, Duluth, Minnesota 55812, USA.

出版信息

J Org Chem. 2010 Mar 19;75(6):2119-22. doi: 10.1021/jo902733f.

DOI:10.1021/jo902733f
PMID:20163086
Abstract

[Bis(trifluoroacetoxy)iodo]perfluoroalkanes C(n)F(2n+1)I(OCOCF(3))(2) (n = 4, 6, 8, 10, 12) can be conveniently prepared by the oxidation of the corresponding perfluoroalkyl iodides with Oxone in trifluoroacetic acid at room temperature and subsequently converted to the stable [hydroxy(tosyloxy)iodo]perfluoroalkanes, C(n)F(2n+1)I(OH)OTs, by treatment with p-toluenesulfonic acid. This general and convenient procedure has been further extended to the synthesis of various [bis(trifluoroacetoxy)iodo]arenes, ArI(OCOCF(3))(2).

摘要

[双(三氟乙酰氧基)碘代]全氟烷烃 C(n)F(2n+1)I(OCOCF(3))(2)(n = 4、6、8、10、12)可通过在室温下用 Oxone 在三氟乙酸中氧化相应的全氟碘化物方便地制备,并且随后通过用对甲苯磺酸处理转化为稳定的[羟基(对甲苯磺酰氧基)碘代]全氟烷烃,C(n)F(2n+1)I(OH)OTs。该通用且方便的程序已进一步扩展到各种[双(三氟乙酰氧基)碘代]芳烃,ArI(OCOCF(3))(2)的合成中。

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