Introduction
<P>(Dichloroiodo)benzene (PhICl
2) 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 PhICl
2 in organic syntheses are summarized. </P>
Preparation
<P>(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]
</P>
Scheme 1
Properties
<P>(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.</P>
