84174-33-4Relevant articles and documents
Tetraphenylphosphonium Tetrafluoroborate/1,1,1,3,3,3-Hexafluoroisopropanol (Ph4PBF4/HFIP) Effecting Epoxide-Initiated Cation-Olefin Polycyclizations
Tian, Yan,Xu, Xin,Zhang, Lin,Qu, Jin
, p. 268 - 271 (2016/02/03)
The use of an excess amount of tetraphenylphosphonium tetrafluoroborate in 1,1,1,3,3,3-hexafluoroisopropanol, which can stabilize the intermediate cation in the reaction, efficiently promoted epoxide-initiated cation-olefin polycyclization reactions with broad functional group tolerance and water and oxygen tolerance.
1,2-Diarylethanols by alternative regioselective reductive ring-opening of 2,3-diaryloxiranes
Blasio, Nadia Di,Lopardo, Maria Teresa,Lupattelli, Paolo
supporting information; experimental part, p. 938 - 944 (2009/07/19)
Non-symmetrical £rans-2,3-diaryloxiranes have been regioselectively opened by catalytic hydrogenation over Pd/C, NaBH4/Pd and [Cp 2TiCl]/H2O. Although in the catalytic hydrogenation reactions the epoxides were mainly opened at the β-carbon with respect to the substituted aryl ring in all cases, with the [Cp2TiCl]/H 2O system the regioselectivity was affected by the electronic properties of the aryl residues, the epoxides being opened on the carbon bearing the most electron-releasing or the least electron-withdrawing group. With the NaBH4/Pd system different regioisomers were obtained depending on the substituents. Starting from enantioenriched epoxides, no loss of optical purity was observed in the alcohols formed.
Generation and Reactions of 2-Alkoxydiphenylcarbenes in Fluid Solution and Rigid Matrices
Tomioka, Hideo,Nakanishi, Keisaku,Izawa, Yasuji
, p. 465 - 470 (2007/10/02)
Irradiation of 2-alkoxydiphenyldiazomethanes 1 in cyclohexane at room temperature produced 3-phenyldihydrobenzofurans 3 presumably as a result of intramolecular C-H insertion of 2-alkoxydiphenylcarbenes 2.Irradiation of compounds 1 in cyclohexane matrix at -196 deg C gave intermolecular C-H insertion products 4 at the expense of benzofurans 3.The formation of products 4 is explicable in terms of H-atom tunnelling to the triplet state of carbenes 2, followed by coupling of the resulting radical pairs.Product ratios 3:4 were somewhat sensitive to the bulk of the alkoxy group at the 2-position.This can be explained in terms of the matrix effect on the relative population of the rotational isomers of the carbene 2.Irradiation of compounds 1 in methanol at room temperature afforded O-H insertion products 5 almost exclusively, whereas irradiation in methanol matrix at -196 deg C gave C-H insertion products 6 along with other products 3 and 5.