102117-75-9Relevant academic research and scientific papers
CATALYTIC REARRANGEMENT OF THE CHLOROALLYL ETHERS OF p-CRESOL
Andreev, N. A.,Bunina-Krivorukova, L. I.,Levashova, V. I.
, p. 345 - 351 (2007/10/02)
The rearrangement of a series of p-cresol ethers (β- and γ-chloro-, β,γ- and β,γ,γ-trichloroallyl), catalyzed by boron trifluoride etherate, was studied.Increase in the number of chlorine atoms in the allyl unit of the ether hinders the rearrangement, and its mechanism changes in the investigated series of ethers from intramolecular -sigmatropic (with inversion of the allyl unit) to intermolecular, which corresponds to electrophilic substitution in the aromatic ring (without inversion).The presence of the chlorine atom at the β position of the allyl unitpromotes rearrangement by a concerted intramolecular mechanism, while a chlorine atom at the γ position promotes rearrangement by an intermolecular stage mechanism.Two chlorine atoms at the γ position give rise mainly to the intermolecular rearrangement path.
CATALYTIC REARRANGEMENT OF THE γ-CHLOROALLYL ETHERS OF PHENOLS
Andreev, N. A.,Bunina-Krivorukova, L. I.,Levashova, V. I.,Aleksandrova, E. K.
, p. 1398 - 1402 (2007/10/02)
The catalytic rearrangement of the γ-chloroallyl ethers of phenol, p- and o-cresol, p- and o-chlorophenol, and 2,4-dichlorophenol takes place by an intermolecular mechanism with the formation of alkenylphenols without inversion of the allylic unit.The transformation of the ethers with a CH3 group (ortho or para) in the benzene ring takes place under milder conditions than that of ethers with a chlorine atom at the same positions.
