Methylthiomethyl ethers, formation during

As mentioned earlier, the most common side reaction during oxidations with the Albright-Goldman protocol is the formation of methylthiomethyl ethers.71 The other common side reaction is the acetylation of the alcohol. These side reactions can be minimized by limiting the amount of Ac20 to about 5 equivalents56 or even less,59 or by lowering the temperature to ca. 5°C.57... 

This is a rare example, in which formation of a methylthiomethyl ether is reported during a... 

The surplus activated DMSO, which remains unreacted after the activation of the alcohol during a Swern oxidation, decomposes on heating, generating the highly reactive species H2C=S(+)-Me (page 97). This species can react with tertiary alcohols present in the molecule, resulting in the formation of a methylthiomethyl ether.237... 

This is a rare case of methylthiomethylation of a primary alcohol during a Swern oxidation. A primary neopentilic alcohol, quite resistant to reaction, was treated under Swern conditions at the temperature of - 10°C. At this temperature, a substantial decomposition of activated DMSO occurred during the activation of the alcohol, resulting in the formation of H2C=S(+)-Me that produced the generation of the methylthiomethyl ether side compound. 

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