Protection of alcohols, aliphatic

Reactions.—Some examples of new methods for ether cleavage have been dealt with in an earlier section (Protection of Alcohols). Aliphatic and aromatic methyl ethers can be cleaved efficiently by an aluminium halide-ethanethiol combination the process has been rationalized according to the hard and soft acid-base principle. Several methods for the (presumed) in situ preparation of trimethylsilyl iodide, a known reagent for the cleavage of ethers (2,131), have been disclosed recently in an effort to circumvent the expense and moisture sensitivity of MeaSil. (Some of these methods have been mentioned earlier in this Report in connection with the conversion of alcohols into alkyl iodides.) Reports include two on trimethylsilyl chloride-sodium iodide, one on phenylseleno-trimethylsilane-iodine [equation (18)], and three on hexamethyldisilane-iodine [equation (jq)] 102,142,143 method has the advantage of... 

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