Vinylic Nucleophilic Substitution [closed]








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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:


[![electrophilic addition to alkoxy alkene](https://i.stack.imgur.com/WwNEW.png)](https://i.stack.imgur.com/WwNEW.png)


I understand that such a reaction has application in polymer chemistry. For example, under the right acidic conditions, methylvinylether will form polyvinylmethylether:


[![polymerization of methylvinylether to polyvineylmethylether under acidic conditions](https://i.stack.imgur.com/9mTYY.png)](https://i.stack.imgur.com/9mTYY.png)


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:


[![hard-hard, soft-soft, and hard-soft interactions](https://i.stack.imgur.com/CpqMK.png)](https://i.stack.imgur.com/CpqMK.png)


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:


[![two electrophilic additions to vinyl ethers](https://i.stack.imgur.com/XMutB.png)](https://i.stack.imgur.com/XMutB.png)


I guess the reaction could be called a **vinylic nucleophilic substitution**.


