27542-97-8Relevant articles and documents
Radical Anion Promoted Chemoselective Cleavage of Csp2-S Bond Enables Formal Cross-Coupling of Aryl Methyl Sulfones with Alcohols
Bai, Jixiang,Wang, Tianxin,Dai, Botao,Liu, Qingchao,Yu, Peiyuan,Jia, Tiezheng
supporting information, p. 5761 - 5765 (2021/08/16)
A novel formal cross-coupling of aryl methyl sulfones and alcohols affording alkyl aryl ethers via an SRN1 pathway is developed. Two marketed antitubercular drugs were efficiently prepared employing this approach as the key step. A dimsyl-anion initiated radical chain process was revealed as the major pathway. DFT calculations indicate that the formation of a radical anion via nucleophilic addition of alkoxide to the aryl radical is the key step in determining the observed chemoselectivity.
Alkylation of phenol by β-pinene in the presence of aluminum phenolate
Chukicheva,Shumova,Kuchin
experimental part, p. 43 - 46 (2012/07/17)
The alkylation of phenol by β-pinene using Al(OPh)3 as a catalyst was studied. It was found that the composition of the products depended on the ratio of starting materials. The principal products were chromane-type ethers with an equimolar ratio of starting materials and an excess of phenol. ortho-Alkylated phenol and an ether with a terpene substituent of bornyl structure were formed with a two-fold excess of β-pinene.
Tandem molecular rearrangement in the alkylation of phenol with camphene
Chukicheva,Spirikhin,Kuchin
, p. 62 - 66 (2008/12/21)
The alkylation of phenol with camphene in the presence of boron trifluoride in glacial acetic acid was accompanied by tandem molecular rearrangement with formation of a mixture of ortho- and para-substituted phenols having 1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yl and 5,5,6-trimethylbicyclo[2.2.1] hept-exo-2-yl substituents. The same products were obtained by rearrangement of 1,7,7-trimethylbicyclo[2.2.1]hept-exo-2-yloxybenzene under analogous conditions. Similar reactions performed in the presence of aluminum phenoxide as catalyst resulted in predominant formation of the corresponding ortho-substituted phenols.