Vinyl group
In
An industrially important example is vinyl chloride, precursor to PVC,[3] a plastic commonly known as vinyl.
Vinyl is one of the
Vinyl polymers
Vinyl groups can polymerize with the aid of a radical initiator or a catalyst, forming vinyl polymers. Vinyl polymers contain no vinyl groups. Instead they are saturated. The following table gives some examples of vinyl polymers.
| Monomer example | Example of resulting polymer |
|---|---|
| Vinyl chloride | Polyvinyl chloride (PVC) |
| Vinyl fluoride | Polyvinyl fluoride (PVF) |
| Vinyl acetate | Polyvinyl acetate (PVAc) |
Synthesis and reactivity
Vinyl derivatives are
- In allyl compounds, where the next carbon is saturated but substituted once, allylic rearrangementand related reactions are observed.
- Allyl Grignard reagents (organomagnesiums) can attack with the vinyl end first.
- If next to an electron-withdrawing group, conjugate addition(Michael addition) can occur.
Vinyl organometallics, e.g. vinyllithium and vinyl tributyltin, participate in vinylations including coupling reactions such as in Negishi coupling.
History and etymology
The radical was first reported by
The modern term was coined by German chemist Hermann Kolbe in 1851, who rebutted Liebig's hypothesis.[5] However even in 1860 Marcellin Berthelot still based the name he coined for acetylene on Liebig's nomenclature and not on Kolbe's.
The etymology of "vinyl" is the Latin vinum = "wine", and the Greek word "hylos" 'υλος (matter or material), because of its relationship with ethyl alcohol.
See also
- Acetylenic
- Allylic/Homoallylic
- Alpha-olefin
- Benzylic
- Propargylic/Homopropargylic
- Vinylogous
References
- ^ Rules for abbreviation of protecting groups p.310
- ^ IUPAC Provisional Recommendations 2004 Chapter 5
- .
- ISSN 2624-8549.
- ^ H. Kolbe (1851), "On the chemical constitution and nature of organic radicals," The Quarterly Journal of the Chemical Society of London, 3 (4) : 369-405; see footnote on page 376.