91084-22-9Relevant academic research and scientific papers
Oxidation of Phenols with Iodine in Alkaline Methanol
Omura, Kanji
, p. 3046 - 3050 (1984)
The use of iodine as an oxidizing agent for phenolic compounds has been explored.The reaction has been conducted in methanol containing such alkali as potassium hydroxide and, depending on the nature of the substituents and on the amount of iodine employed, leads to iodination, oxidation to give a stable phenoxy radical, oxidative dimerization, or benzylic oxidation.In general the reaction proceeds smoothly at room temperature, and under appropriate conditions yields of products are good to excellent.Oxidative dimerization of 2,4- and 2,6-di-tert-butylphenols invol-ves iodination followed by iodine-catalyzed dimerization.The oxidation of 4-methylphenols with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone in methanol has been carried out for comparison.
Phenolic oxidation of o,o'-dihalogenated phenols
Takahashi, Masakatsu,Konishi, Hironori,Iida, Satoshi,Nakamura, Kensuke,Yamamura, Shosuke,Nishiyama, Shigeru
, p. 5295 - 5302 (2007/10/03)
A detailed inspection of phenolic oxidation products derived from the o,o'-dihalogenated cresol derivatives (1a - 1e) indicated that the bromo and chloro substituents promoted the oxidation leading to the corresponding diaryl ethers, whereas the iodo derivatives provided the diaryls. Selective reduction of 6d and its tyrosine derivative afforded the corresponding diaryl ethers carrying two chlorine atoms (14, 15). Interpretation of the selectivity of the phenolic oxidation was attempted by employing theoretical calculations.
