Hydroxyl exchange

Brenan J.M. (1994) Kinetics of fluorine, chlorine and hydroxyl exchange in fluorapatite. Chem. Geol. 110, 195-210. 

The preparation starts much as does that of (3-blockers, by reaction of the phenol (5-1) with epichlorohydrin with the important difference that the reaction is conducted with a controlled amount of the epoxide. The initially formed glycydil ether (5-2) thus reacts with a second phenoxide ion to afford the double ether of glycerol (5-3). This product is then condensed with diethyl oxalate in the presence of a base. The initially formed acylation product (5-4) then undergoes internal hydroxyl exchange to form a coumarone ring. The structure shown for the initial... 

Finally the secondary benzylic hydroxyl exchanges a hydrogen bond with Ser . 

Photolysis at 254 nm, rt, 30 min, CH3CN, 75-92% yield. Cleavage occurs by trans to cis isomerization followed by hydroxyl exchange to release the alcohol. Cleavage of the naphthyl analog occurs at 350 nm. ... 

Eyring and Wadsworth (50) and Little (51) present spectroscopic evidence that thiols bond to ZnO surfaces and xanthates bond to PbS surfaces by way of hydroxyl-exchange reactions in which metal-sulfide bonds are formed, and metal-hydroxyl bonds are broken during adsorption. We expect that trends exhibited in the relative stabilities of amino acid and hydroxo complexes of various dissolved cations should parallel trends in the relative reactivities and adsorption free energies, should this type of bonding control adsorption. 

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