While reading "Francis A. Carey, Richard J. Sundberg - Advanced Organic Chemistry Part A. Structure and Mechanisms-Springer (2007)", I came across the following schematic for addition of electrophiles to vinyl ethers:
I understand that such a reaction has application in polymer chemistry. For example, under the right acidic conditions, methylvinylether will form polyvinylmethylether:
Under what conditions will the electrophile react with the lone-pair of oxygen instead of the $\beta$-Carbon?
In another section, I found that hard-hard and soft-soft interactions are preferred over hard-soft interactions:
Many questions arise from reading this. Is the lone pair on the oxygen atom hard or soft? And accordingly, what kind of electrophile should be used? Do stearic factors play a role?
It has been pointed out in the comments that addition of electrophile to oxygen is a reversible and non-productive. What I was thinking was something like this:
I guess the reaction could be called a vinylic nucleophilic substitution.
