Iodosobenzene

Iodosobenzene is an organic compound with the empirical formula C6H5IO. It is a white solid that is used as a reagent in organic chemistry. Iodosobenzene is often used as an oxidizing agent.

Structure and Bonding

Iodosobenzene has a planar molecular structure with an I=O bond length of 1.632 Å and a C-I bond length of 2.131 Å. The I=O bond is shorter than the typical I-O bond length of 1.757 Å, indicating the presence of a double bond. The C-I bond length is longer than the typical C-I bond length of 2.117 Å, indicating that the bond is weaker than a typical C-I bond.

Synthesis

Iodosobenzene can be synthesized from iodobenzene by oxidation with oxygen in the presence of a copper catalyst. The reaction proceeds via the formation of iodobenzene diacetate, which is then decomposed to iodosobenzene and acetic acid.

Reactions

Iodosobenzene is a versatile oxidizing agent that is used in a variety of organic reactions. It can oxidize alcohols to aldehydes or ketones, and it can oxidize amines to nitro compounds. It can also be used in the Sandmeyer reaction to convert amines to diazonium salts, which can then be converted to a variety of other functional groups.

Safety

Iodosobenzene is a strong oxidizing agent and should be handled with care. It can cause burns and eye damage, and it may be harmful if swallowed or inhaled.