Nucleophilic attack of intramolecular hydroxyl groups on electron-rich aromatics using hypervalent iodine(III) oxidation was written by Hata, Kayoko;Hamamoto, Hiromi;Shiozaki, Yukiko;Caemmerer, Simon B.;Kita, Yasuyuki. And the article was included in Tetrahedron in 2007.Electric Literature of C11H16O3 This article mentions the following:
The hypervalent iodine(III) reagent, phenyliodine bis(trifluoroacetate) (PIFA)-mediated oxidative nucleophilic substitution of electron-rich aromatics involving aromatic cation radical intermediates was utilized in the direct aromatic carbon-oxygen bond formation reaction, and a novel and simple synthetic method for chroman derivatives was developed. E.g., in presence of PIFA, intramol. oxidative cyclization of hydroxy-substituted benzene I gave up to 55% chroman II. As an extension of this methodol., a facile access to spirodienone derivatives was also achieved. In the experiment, the researchers used many compounds, for example, 3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3Electric Literature of C11H16O3).
3-(3,4-Dimethoxyphenyl)propan-1-ol (cas: 3929-47-3) 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. Autoxidation is the spontaneous oxidation of a compound in air. In the presence of oxygen, ethers slowly autoxidize to form hydroperoxides and dialkyl peroxides. If concentrated or heated, these peroxides may explode. To prevent such explosions, ethers should be obtained in small quantities, kept in tightly sealed containers, and used promptly.Electric Literature of C11H16O3
Referemce:
Ether – Wikipedia,
Ether | (C2H5)2O – PubChem