Question

A recent report (ca. 2003) in Organic Synthesis reported a simple means of iodination of alkanes. The protocol called for tert-butyl hypoiodite and the alkane that is halogenated as the solvent for the reaction (shown below). Propose a reasonable mechanism based on monohalogenation of alkanes. Additionally, propose a rationale for why this is possible when iodination using elemental iodine under the same conditions is not.

Answer 1

Drawn below is the radical mechanism for the iodination of alkane chain using tert-butyl hypoiodate reagent as the iodinating reagent.

the reagent here is more labile and easily promotes iodination unlike elemental iodine which is very stable in its form and thus this reagent is preferred for iodination.

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