Iodination of Methylated Anisoles: Unusual Aryl Methyl Replacements and Oxidations was written by Panetta, Charles A.;Fang, Zheng;Mattern, Daniell L.. And the article was included in Journal of Organic Chemistry in 1995.Formula: C8H9IO This article mentions the following:
The treatment of methylated anisoles with iodine, periodic acid, sulfuric acid, and aqueous acetic acid has resulted in iododemethylations and/or aryl Me oxidations in addition to the expected mono- and diiodinations of the aromatic ring. Four dimethylanisoles and o-methylanisole were treated under identical conditions. Iododemethylations were observed in three of the four dimethylanisoles and aryl Me oxidations to benzaldehydes occurred with o-methylanisole and two of the dimethylanisoles. No precedence could be found for either of these reactions under the exptl. conditions employed. Several possible mechanisms are discussed for these transformations. Some exptl. evidence suggests that Me oxidation to a benzaldehyde could be a prerequisite for an iododemethylation via an iodonium ion-assisted reverse Gattermann-Koch reaction: single-electron-transfer or classical electrophilic mechanisms are also consistent with the iododemethylations. In the experiment, the researchers used many compounds, for example, 4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2Formula: C8H9IO).
4-Iodo-1-methoxy-2-methylbenzene (cas: 75581-11-2) belongs to ethers. Ether is less polar than esters, alcohols or amines because of the oxygen atom that is unable to participate in hydrogen bonding due to the presence of bulky alkyl groups on both sides of the oxygen atom. But ether is more polar than alkenes. Electron-deficient reagents are also stabilized by ethers. For example, borane (BH3) is a useful reagent for making alcohols. Pure borane exists as its dimer, diborane (B2H6), a toxic gas that is inconvenient and hazardous to use. Borane forms stable complexes with ethers, however, and it is often supplied and used as its liquid complex with tetrahydrofuran (THF).Formula: C8H9IO
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem