P-aryloxy alcohols

Bai W-J, Xie J-H, Li Y-L, Liu S, Zhou Q-L. Enantioselective synthesis of chiral p-aryloxy alcohols by ruthenium-catalyzed ketone hydrogenation via dynamic kinetic resolution (DKR).A Jv. Synth. Catal. 2010 352(l) 81-84. 

The diastereomerically pure chlorides 73a and 73b afforded the corresponding P-substitution products on reaction with nucleophiles. Thus 73a and 73b could be converted readily into the corresponding alkoxy-derivatives on treatment with an alcohol in the presence of triethylamine and into aryloxy-derivatives upon treatment with the sodium salt of the appropriate phenol at room temperature. Replacement of chlorine by an alkoxy- or aryloxy-group occurred with retention of configuration, e.g., 73a gave 74a, 75a, and 76a. Similarly, 74b and 75b could be obtained from 73b (Scheme 24) [32, 38, 54],... 

L. S. Klimenko, N. P. Gritsan, and E. P. Fokin, Kinetics and mechanism of the reaction between photoinduced 9-aryloxy-l,10-anthraquinones and alcohols, Izv. Akad. Nauk SSSR, Ser. Khim. Nauk N3, 366-370 (1990) (Russ.). 

Compound 468 readily replaced 1-0-acetyl group for a number of alkoxy, aryloxy, and thioalkoxy groups in reactions with alcohols, phenols, or thiols in the presence of p-toluenesulfonic acid. In the case of alcohols and phenols, the reaction was stereospecific and 3-anomers (472) were formed. With thiols, both anomeric thioglycosides (473) were obtained in about equal proportions. 

Decarbo>ylation of a-(oo-carbo grallg l)-p-ketoesters (44) by photoinduced electron transfer leads to one-carbon expanded y-ketoesters and bicyclic alcohols.Irradiation of aqueous alkaline solutions of 2-aryloxy- or 2-aryl-acetic acids at 300 nm in the presence of Selectfluor results in fluorodecarboxylation. Decarbojq lation of aliphatic carboxylic acids or iV-(t-buto)ycarbonyl)amino acids by means of oxidative electron transfer using catalytic amounts of photosensitisers leads to free radicals that can by trapped by actylonitrile. ... 

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