117699-48-6Relevant academic research and scientific papers
Base-Mediated O-Arylation of Alcohols and Phenols by Triarylsulfonium Triflates
Ming, Xiao-Xia,Tian, Ze-Yu,Zhang, Cheng-Pan
supporting information, p. 3370 - 3379 (2019/11/03)
A mild and efficient protocol for O-arylation of alcohols and phenols (ROH) by triarylsulfonium triflates was developed under transition-metal-free conditions. Various alcohols, including primary, secondary and tertiary, and phenols bearing either electron-donating or electron-withdrawing groups on the aryl rings were smoothly converted to form the corresponding aromatic ethers in moderate to excellent yields. The reactions were conducted at 50 or 80 °C for 24 h in the presence of a certain base and showed good functional group tolerance. The base-mediated arylation with asymmetric triarylsulfonium salts could selectively transfer the aryl groups of sulfoniums to ROH, depending on their inherent electronic nature. The mechanistic studies revealed that the reaction might proceed through the nucleophilic attack of the in situ formed alkoxy or phenoxy anions at the aromatic carbon atoms of the C?S bonds of triarylsulfonium cations to furnish the target products.
Thermally Induced Rearrangement of Thiopheniobis(alkoxycarbonyl)methanides
Bowles, Timothy,Gillespie, Roger J.,Porter, Alexander E. A.,Rechka, Josef A.,Rzepa, Henry S.
, p. 803 - 808 (2007/10/02)
Thiopheniobis(alkoxycarbonyl)methanides undergo intramolecular rearrangement when heated, to give 2H-thiopyrans as thermally unstable kinetic products.When the methanides are subjected to prolonged heating thiophene-2-malonates are produced as the major rearrangement products.A mechanism for these transformations is advanced in an attempt to rationalise the known reactivity of thiophene and its derivatives towards diazoalkanes.
