13031-43-1Relevant articles and documents
Solvent and temperature effects in the free radical aerobic oxidation of alkyl and acyl aromatics catalysed by transition metal salts and N-hydroxyphthalimide: New processes for the synthesis of p-hydroxybenzoic acid, diphenols, and dienes for liquid crystals and cross-linked polymers
Minisci, Francesco,Recupero, Francesco,Cecchetto, Andrea,Gambarotti, Cristian,Punta, Carlo,Paganelli, Roberto,Pedulli, Gian Franco,Fontana, Francesca
, p. 163 - 168 (2004)
The aerobic oxidation of 4,4′-diisopropyldiphenyl and 2,6-diisopropylnaphthalene, catalysed by N-hydroxyphthalimide and Co(II) salts, leads to the corresponding tertiary benzyl alcohols with high conversion and selectivity under mild conditions (temperature 30-60°C and atmospheric pressure). Solvent and temperature effects, as resulting from the pioneering work of C. Walling, and more recently from the conclusive resolution of K. U. Ingold and co-workers on a quantitative kinetic basis, strongly affect the selectivity of the aerobic oxidation. This is related to the ratio between the rate of β-scission of the alkoxyl radical, which leads to acetophenone derivatives, and the rate of hydrogen atom abstraction, leading to tertiary benzyl alcohols. These latter are efficiently converted either to diphenols for the production of liquid crystals, by reaction with H2O2, or to dienes, useful as cross-linking agents, by dehydration. The aerobic oxidation of p-hydroxyacetophenone catalysed by Mn(NO3)2 and Co(NO3)2 leads with high selectivity to p-hydroxybenzoic acid, a useful monomer for liquid crystals.
Electrochemical Aerobic Oxidative Cleavage of (sp3)C-C(sp3)/H Bonds in Alkylarenes
Liu, Shuai,Liu, Zhong-Quan,Shen, Tong,Shen, Xu,Wang, Nengyong,Wu, Jintao,Yang, Le,Zhao, Jianyou
, p. 3286 - 3295 (2022/03/14)
An electrochemistry-promoted oxidative cleavage of (sp3)C-C(sp3)/H bonds in alkylarenes was developed. Various aryl alkanes can be smoothly converted into ketones/aldehydes under aerobic conditions using a user-friendly undivided cell setup. The features of air as oxidant, scalability, and mild conditions make them attractive in synthetic organic chemistry.
An efficient and practical aerobic oxidation of benzylic methylenes by recyclable: N -hydroxyimide
Wang, Jian,Zhang, Cheng,Ye, Xiao-Qing,Du, Wenting,Zeng, Shenxin,Xu, Jian-Hong,Yin, Hong
, p. 3003 - 3011 (2021/01/28)
An efficient and practical benzylic aerobic oxidation catalyzed by cheap and simple N-hydroxyimide organocatalyst has been achieved with high yields and broad substrate scope. The organocatalyst used can be recycled and reused by simple workup and only minute amount (1 mol% in most cases) of simple iron salt is used as promoter. Phenyl substrates with mild and strong electron-withdrawing group could also be oxygenated in high yields as well as other benzylic methylenes. Influence of substituents, gram-scale application, catalysts decay and general mechanism of this methodology has also been discussed. This journal is
METHOD FOR OXIDATIVE CLEAVAGE OF COMPOUNDS WITH UNSATURATED DOUBLE BOND
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Paragraph 0071, (2021/07/10)
A method for oxidative cleavage of a compound with an unsaturated double bond is provided. The method includes the steps of: (A) providing a compound (I) with an unsaturated double bond, a trifluoromethyl-containing reagent, and a catalyst; wherein, the catalyst is represented by Formula (II): M(O)mL1yL2z??(II);wherein, M, L1, L2, m, y, z, R1, R2 and R3 are defined in the specification; and(B) mixing the compound with an unsaturated double bond and the trifluoromethyl-containing reagent to perform an oxidative cleavage of the compound with the unsaturated double bond by using the catalyst in air or under oxygen atmosphere condition to obtain a compound represented by Formula (III):
