Chloral is not further oxidized by chlorine, which is why it is so easy to make. Only when alkali is added does it decompose into chloroform and
formate. So presumably triiodoacetaldehyde would behave similarly. But the problem is, the diiodoacetaldehyde might not be further oxidized due to the
carbonyl withdrawing electrons from the hydrogen. This doesn't mean that triiodoethanol doesn't exist, but it would make it harder to produce than the
trichloro or tribromo compound, since enol iodination is not available.
Possibly, the reaction of ethanol with iodine monochloride would give triiodoacetaldehyde, this later being reduced to triiodoethanol. The same trick
works for arene iodinations. |