Introduction
(Dichloroiodo)benzene (PhICl2) was first prepared in 1886; its chemistry then became an intensely studied topic because of its wide application as an effective chlorinating or oxidizing agent in various organic reactions.
[1]
As a chlorinating agent, (dichloroiodo)benzene can be applied not only to the addition of chlorine to alkenes, but also to the chlorination with other substrates, such as alkanes, ethers, esters, thioethers, ketones, sulfoxides, steroids, etc., with moderate to high yields.
[1]
[2]
(Dichloroiodo)benzene can oxidize aldoximes and ketoximes to nitrile oxides
[3]
and ketones,
[4]
respectively in good yields. In this spotlight, recent applications using PhICl2 in organic syntheses are summarized.
Preparation
(Dichloroiodo)benzene was prepared by bubbling chlorine gas through a solution of iodobenzene in chlorinated solvents,
[5]
which had been applied to an industrial-scale preparation (Scheme
[1]
).
[6]
Scheme 1
Properties
(Dichloroiodo)benzene exists as yellow crystalline solid with mp 110-112 °C. It is not stable on long standing, which means that it is normally prepared and used fresh for subsequent applications.
