3.3.6 Anionic Polymerization

The anionic polymerization of butadiene, isoprene and styrene using the catalysis of alkyllithium is a major industrial use (Scheme 14).

Scheme 14

3.3.7. Named Organic Reactions

3.3.7.1 [1,2]-Wittig Rearrangement

Ethers with organolithium proceed the [1,2]-Wittig rearrangement to yield alcohols (Scheme 15). The groups R and R' may be alkyl, aryl or vinyl. The migration follows the order allyl > benzyl > ethyl > methyl > phenyl.

Scheme 15

Examples:

3.3.7.2 [2,3]-Wittig Rearrangement

It is a sigmatropic rearrangement of a α -deprotonated ally ether (Scheme 17).

Scheme 17