82499-75-0Relevant academic research and scientific papers
EFFECT OF NUCLEOPHILIC ADDITIONS ON THE VARIATION OF THE ORTHO-PARA ORIENTATION DURING THE CATALYTIC REARRANGEMENT OF ALKENYL ARYL ETHERS
Feoktistov, V. M.,Bunina-Krivorukova, L. I.,Aleksandrova, E. K.
, p. 1977 - 1984 (2007/10/02)
The catalytic rearrangement of γ-chloro-γ-methyl- and γ,γ-dimethylallyl ethers of o- and p-cresols in the presence of various amounts (0.25-10 moles) of the related nucleophiles (o- and p-cresol) was investigated.The contribution from intermolecular alkenylation of the related nucleohile increases substantially with increase in its amount from 0.25 to 4 moles.Further increase (to 10 moles) gives a small increase in the degree of alkenylation.Comparison of the products from ortho-para-alkenylation during rearrangement and during direct alkenylation of the mixtureof cresols by allyl halides makes it possible to suppose that the catalytic rearrangement of the ethers can take place both by an intermolecular mechanism and, in parallel, by an intramolecular (non-Claissen) mechanism with the formation of the same products - with retention of the structure of the allyl unit in the initial ether.
