14035-38-2Relevant academic research and scientific papers
Iodide as an activating agent for acid chlorides in acylation reactions
Wakeham, Russell J.,Taylor, James E.,Bull, Steven D.,Morris, James A.,Williams, Jonathan M. J.
supporting information, p. 702 - 705 (2013/04/11)
Acid chlorides can be activated using a simple iodide source to undergo nucleophilic attack from a variety of relatively weak nucleophiles. These include Friedel-Crafts acylation of N-methylpyrroles, N-acylation of sulfonamides, and acylation reactions of hindered phenol derivatives. The reaction is believed to proceed through a transient acid iodide intermediate.
Oxygenation of 2,6-Di-tert-butylphenols Bearing an Electron-Withdrawing Group in the 4-Position
Nishinaga, Akira,Shimizu, Tadashi,Toyoda, Yasushi,Matsuura, Teruo,Hirotsu, Ken
, p. 2278 - 2285 (2007/10/02)
Co(Salpr), a five-coordinate cobalt (II) Schiff base complex, has been found to promote oxygenation of 2,6-di-tert-butylphenols bearing an electron-withdrawing group in the 4-position, leading to dioxygen incorporation exclusively into the ortho position of the phenols. 4-Acyl-2,6-di-tert-butylphenols (1) and their oxime O-methyl ethers (2) gave the corresponding 6-hydroperoxy-2,4-cyclohexadienone derivatives 3 and 4 quantitatively.Schiff bases 10 derived from 3,5-di-tert-butyl-4-hydroxybenzaldehyde, on the other hand, gave unexpected products, 1,2-dihydropyridine derivatives 11, cyclopentadienone 12, and epoxy-o-quinol 13.The structure of dihydropyridine 11a was determined by X-ray analysis. 2,6-Di-tert-butyl-4-cyanophenol gave 2,5-di-tert-butyl-3-cyano-2,4-cyclopentadienone in good yield.The formation of these products can be understood to result from intramolecular decomposition of the corresponding o-peroxidic intermediate.Phenols 2 were readily oxygenated in t-BuOH containing t-BuOK to give epoxy-o-quinols 7 in excellent yield, although the other phenols examined were unsusceptible to oxygenation under various basic conditions.
OXYGENATION OF 2,6-DI-t-BUTYLPHENOLS BEARING ELECTRON-WITHDRAWING GROUP AT 4-POSITION MEDIATED BY CO(II)-SCHIFF BASE COMPLEX
Nishinaga, A.,Shimizu, T.,Matsuura, T.
, p. 5293 - 5296 (2007/10/02)
4-Acyl-2,6-di-t-butylphenols except 3,5-di-t-butyl-4-hydroxybenzaldehyde were oxygenated in the presence of Co(Salpr) exclusively at the ortho position to give the corresponding 3,5-di-t-butyl-6-hydroperoxy-2,4-cyclohexadienone derivatives in quantitative
