Question

I was wondering how the reaction between neopentyl alcohol and triphenylphosphite/methyl iodide looks like from a mechanistic point of view.

It should involve the formation of a phosphonium iodide salt, which can then use the phosphorus' oxophilicity; however, for that to work, the alcohol needs to act as a nucleophile, which in my opinion is not feasable, as alcohols in general are weak nucleophiles.

Answer 1

The reaction between neopentyl alcohol and triphenylphosphite/methyl iodide proceeds through the Gabriel synthesis mechanism, where the alcohol acts as a nucleophile.

Step-by-step explanation:

The reaction between neopentyl alcohol and triphenylphosphite/methyl iodide can proceed through a mechanism known as the Gabriel synthesis. In this reaction, the alcohol acts as a nucleophile and attacks the carbon atom of the triphenylphosphite, displacing the iodide ion.

This results in the formation of a phosphonium iodide salt. The alcohol can then deprotonate the phosphonium cation, leading to the formation of the desired product.