Alkyl hypoiodites preparation

Alkyl hypochlorites and hypobromites are relatively stable molecules alkyl hypoiodites can only be prepared in situ, usually by the reaction of alcohols with metal acetates or oxides and iodine or by the reaction of alcohols with a hypervalent iodine compound and iodine.1319 Alkyl hypochlorites and hypoiodites can be utilized in reactions that parallel those of the organic nitrites (Barton reaction Section 6.4.2). For example, the photochemistry of the steroidal hypoiodite 497, prepared by the reaction of the corresponding alcohol with iodine oxide (I2O) generated from mercury(II) oxide and molecular iodine in situ, affords a new five-membered ring via an O I bond fission, 1,5-hydrogen abstraction and substitution (Scheme 6.244).1353... 

Although alkyl hypochlorites and hypobromites are isolable species, alkyl hypoiodites are not isolable. They can only be prepared in situ, either by the reaction of alcohols with metal acetates or oxide and iodine in solution, or by the reaction of alcohols with a hypervalent iodine compound and iodine in... 

---