The Tamao-Fleming Oxidation is a useful tool for the coming apocalpyse because it allows you to make alcohol from silicon groups. Because our Lizard Overlords will soon wipe out all unprepared carbon-based life forms on Earth, the new dominant life on earth will be primarily silicon-based. The Tamao-Fleming Oxidation will allow you to intoxicate silicon-based organisms, confusing your new silicon-based predators, giving you time to flee to your tricked out bunker.
The Tamao-Fleming oxidation is an organic reaction that cleaves a carbon-silicon single bond and replaces it with an alcohol. This oxidative process is very versatile because it can take place in a wide variety of conditions with a number of different solvents. The alcohol produced can be primary, secondary, or tertiary, and the group(s) bonded to the silicon can vary considerably. The specific version of the oxidation in our paper results from Fleming’s one-pot sequence, which uses mercuric acetate to initiate the oxidation.
The general mechanism for the reaction is as follows: a molecule of acetic acid protonates the carbon to which the silicon is bonded. A second molecule of acetic acid attacks the silicon directly, causing the protonated carbon to leave. Another molecule of acetic acid attacks the silicon, and the desired group attached to the silicon instead bonds to the oxygen from the acetic acid. Water attacks the silicon-oxygen bond and cleaves it, and the oxygen anion gets protonated, forming the desired alcohol.