Menkir, Mengistu Gemech published the artcileThe role of cesium fluoride in aryl propargyl ether Claisen rearrangement and its mechanistic elucidation: a theoretical study, Formula: C10H10O2, the main research area is cesium fluoride aryl propargyl ether Claisen rearrangement mechanistic theor.
The role of cesium fluoride (CsF) in aryl propargyl ether Claisen rearrangement and its mechanistic pathway were studied in gas and solvent phase using the d. functional theory implemented in Gaussian 09. Results indicate that the [3,3]-sigmatropic rearrangement is the rate-limiting step with ΔG‡ value of 37.1 kcal/mol in solvent phase. Also, the enolization of α-allenylketone intermediate (Int1-CsF) has a higher free energy barrier, which implies that the formation of benzopyran is not favored in the presence of CsF. However, the abstraction of the α-hydrogen atom in Int1-CsF with CsF shows a very low free energy barrier and is the most favored pathway for aryl propargyl ether Claisen rearrangement in the presence of CsF to form benzofuran. In the case of substituted aryl propargyl ethers, a methoxy group on the benzene ring lowers the activation barrier. The HOMO-LUMO, conformational and NBO anal. indicate that increasing Me substitution on the propargyl residue enhances the rearrangement reaction.
Structural Chemistry published new progress about [3,3]-Sigmatropic rearrangement (rds). 13391-27-0 belongs to class benzofurans, name is 5-Methoxy-2-methylbenzofuran, and the molecular formula is C10H10O2, Formula: C10H10O2.
Referemce:
Benzofuran – Wikipedia,
Benzofuran | C8H6O – PubChem