The reaction of phenyl-substituted allyl chlorides and phenyllithium and the application of the CIDNP technique to the reaction of allylic halides and phenyllithium
Farrell, Francis Elizabeth
Lewis, E. S.
Master of Arts
The reaction of phenyllithium and phenyl-substituted allylic chlorides were investigated. Product distribution indicated that various proportions of coupling, a-elimination followed by cyclopropene formation, halogen-metal exchange, and polymerization reactions had taken place. Plausible mechanisms leading to the various products were discussed. The salt-effect usually accompanying reactions involving organolithium compounds was observed. The CIDNP technique was used in an attempt to detect a possible radical intermediate in the reaction of allylic halides and phenyllithium, but none was found.