29277-50-7Relevant academic research and scientific papers
Water-Accelerated Claisen Rearrangements
Wipf, Peter,Rodriguez, Sonia
, p. 434 - 440 (2007/10/03)
Allyl aryl ethers undergo accelerated Claisen and [1,3] rearrangements in the presence of a mixture of trialkylalanes and water or aluminoxanes. The ratio of ortho-, meta-, and pora-Claisen products depends to a large extent on the presence of water and to a much lesser extent on the nature of the alane.
THERMAL AND CATALYTIC REARRANGEMENTS OF 4-(1,1-DIMETHYL-2-PROPENOXY)TOLUENE
Aleksandrova, E. K.,Bunina-Krivorukova, L. I.
, p. 742 - 745 (2007/10/02)
During the thermal and catalytic rearrangements of 4-(1,1-dimethyl-2-propenoxy)toluene the Claisen phenol, with inversion of the allyl unit, i.e., 4-methyl-2-(3-methyl-2-butenyl)phenol, is formed primarily.The formation of 2-methyl-2-(3-methyl-2-butenyl)phenol in the catalytic rearrangement with the introduction of o-cresol into the reaction zone shows that this rearrangement has partly intermolecular character.Consequently, the Claisen phenol can also be obtained by an intermolecular path, where this phenol is the most thermodynamically stable isomer.
EFFECT OF STRONG NUCLEOPHILE ON THE DIRECTION OF TRANSFORMATION IN ALKENYL ARYL ETHERS DURING CATALYTIC REARRANGEMENT
Bunina-Krivorukova, L. I.,Feoktistov, V. M.,Aleksandrova, E. K.,Bal'yan, Kh. V.
, p. 745 - 750 (2007/10/02)
The results from the introduction of tetrahydrothiophene into the reaction zone during the catalytic rearrangements of alkenyl aryl ethers demonstrate the possibility of a change in the direction of transformation of the ether from -sigmatropic rearrangement to intermolecular alkenylation of a concurrent strong nucleophile.The heterolytic character of the catalytic intermolecular rearrangement (alkenylation) was confirmed by the formation of alkenylsulfonium salts, the structure of the allyl unit which corresponded to the most thermodynamically stable isomer.
