And cleavage of ethers

Monochloroborane-dimethyl sulfide is an effective reagent for the chemo- and regiose-lective opening of oxiranes and cleavage of ethers (equation 180)1111. 

There are cases when a substrate is not used for growth, but is metabolized in the presence of a second substrate that is used to support microorganism reproduction. This type of transformation is called cometabolism. Cometabolic conversions that apparently involve a single enzyme include hydroxylations, oxidations, denitrations, deaminations, hydrolyses, acylations, and cleavages of ether bonds. Many of these conversions are complex and involve several enzymes. This may be explained by the existence of enzymes that perform a single type of reaction, but which act on a series of closely related molecules. 

Formation and Cleavage of Ethers in Acidic Media. When alcohols are treated with acids, dehydration (p. 105) or etherification often occurs. Diethyl ether, for example, is prepared commercially by passing ethanol into a mixture of sulfuric acid and alcohol maintained at 140°. By modifying this method somewhat, satisfactory yields of certain mixed ethers have been obtained.4 In other instances etherification proceeds extremely readily. Triphenylcarbinol is etherified by boiling with methanol5 (unless it is carefully freed of traces of acid),6 and benzhydrol is reported to form dibenzhydryl ether by refluxing it with water.7 Again, traces of acid are probably responsible for reaction. 

Br0nsted acidic ionic liquids have been successfully applied to a variety of reactions including esterification of carboxylic acids [55], protection of aldehydes and ketones [56], and cleavage of ethers [57], 3-Methylimidazolium hydrogen sulfate ([hmim][HSO ]) is a Brpnsted acidic ionic liquid that applied for the oxidation of... 

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