79251-44-8Relevant academic research and scientific papers
An efficient catalyst for ring opening of epoxides with phenol and thiophenol under solvent-free conditions
Lu, Hong-Fei,Zhou, Jun-Tao,Cheng, He-Long,Sun, Lei-Lei,Yang, Fei-Fei,Wu, Run-Ze,Gao, Yu-Hua,Luo, Zhi-Bin
, p. 11174 - 11184 (2014/01/06)
An efficient and rapid procedure for ring opening reaction of various epoxides with phenol and thiophenol derivatives was developed. The procedure can be obtained at room temperature under solvent-free condition in presence of (C4H12N2)2[BiCl6] Cl·H2O (1 mol %). This catalyst can be reused several times without significant loss of activity.
Nucleophilic substitution reactions of sulfur-substituted cyclohexanone acetals: An analysis of the factors controlling stereoselectivity
Billings, Susan B.,Woerpel
, p. 5171 - 5178 (2007/10/03)
The reactions of cyclohexanone acetals substituted with thiophenyl groups (and other heteroatoms) at C-2 demonstrate the powerful influence that these substituents have on the stereoselectivity of nucleophilic substitution reactions. The trans selectivities of these reactions correlate with the behavior of the corresponding ketones. These experiments lend support to the possibility that the reactions of the acetals, which proceed via oxocarbenium ions, are operating under Felkin-Anh control.
CONVENIENT ENANTIOSELECTIVE HYDROLYSIS OF RACEMIC trans-1-ACETOXY-2-ARYLOXYCYCLOHEXANES BY CRUDE PIG LIVER ACETONE POWDER (PLAP)
Basavaiah, D.,Krishna, P. Rama,Bharathi, T. K.
, p. 4347 - 4348 (2007/10/02)
Crude pig liver acetone powder (PLAP) hydrolyzes trans-1-acetoxy-2-aryloxycyclohexanes enantioselectively to produce the corresponding alcohols in high optical purities.
Conversion of One Hydroxy Group in a Diol to a Phenyl Ether with Triphenylbismuth Diacetate, a New Glycol Reaction Showing Strong Axial Preference in Six-Membered Rings
David, Serge,Thieffry, Annie
, p. 441 - 447 (2007/10/02)
After being refluxed for a few hours, a dichloromethane solution of a diol with triphenylbismuth diacetate gave in most cases excellent yields of a monophenyl ether.No diphenylated products were found.Tertiary hydroxy groups were only phenylated in bis tertiary diols, and then in poor yield.Increasing the distance between the hydroxy groups up to six carbon atoms decreased the speed of the reaction which nevertheless was still preparatively useful.Diols in flexible rings behaved like their acyclic counterparts.The course of the reaction was also examined with someconformationally rigid molecules: trans-4-tert-butyl-cis-2-hydroxycyclohexanol, trans-4-tert-butyl-trans-2-hydroxycyclohexanol, cholestane-2α,3α-diol, cholestane-2α,3β-diol, and pyranoside derivatives with the α-D-gluco, α-D-manno, α-D-galacto, and α-D-allo configurations.The phenylations of cis-diols were strongly regioselective for axial epimers, while those of trans, bis equatorial diols were undiscriminate and often much slower.A feasible general mechanism is proposed to explain these results.
SELECTIVE PHENYLATION IN MILD CONDITIONS OF ONE HYDROXY GROUP IN GLYCOLS WITH TRIPHENYLBISMUTH DIACETATE: A NEW SPECIFIC GLYCOL REACTION.
David, Serge,Thieffry, Annie
, p. 5063 - 5066 (2007/10/02)
Refluxing for 4-5 h a dichloromethane solution of diol in the presence of an equimolecular quantity of triphenylbismuth diacetate gave the monophenyl ether in good to excellent yield.
