81455-01-8Relevant articles and documents
ASYMMETRYSCHE KATALYSEN. XXXII. ENANTIOSELEKTIVE PHENYLIERUNG VON cis-CYCLOHEXAN-1,2-DIOL UND meso-BUTAN-2,3-DIOL
Brunner, Henri,Obermann, Uwe,Wimmer, Peter
, p. C1 - C3 (1986)
The monophenylation of cis-cyclohexan-1,2-diol and meso-butan-2,3-diol with triphenylbismuth diacetate gives cis- 1-phenoxycyclohexan-2-ol and2-phenoxybutan-3-ol, respectively.In the presence of catalysts consisting of Cu(OAc)2 and opticallly active pyridine oxazoline ligands, optical inductions of up to 30 percent ee are attained.
Copper(II) pivalate/oxone: An improved promoter system for aryl transfer via organo-bismuth reagents
Sheppard, George S.
, p. 1207 - 1210 (2007/10/03)
As part of a medicinal chemistry project, it was necessary to develop effective conditions for the arylation of hydroxyl groups prone to elimination. Modest success was achieved using triarylbismuth reagents under literature conditions. Based on the side
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.