101934-23-0Relevant articles and documents
Catalytic Ring-Opening of Cyclic Alcohols Enabled by PCET Activation of Strong O-H Bonds
Yayla, Hatice G.,Wang, Huaiju,Tarantino, Kyle T.,Orbe, Hudson S.,Knowles, Robert R.
, p. 10794 - 10797 (2016)
We report a new photocatalytic protocol for the redox-neutral isomerization of cyclic alcohols to linear ketones via C-C bond scission. Mechanistic studies demonstrate that key alkoxy radical intermediates in this reaction are generated via the direct homolytic activation of alcohol O-H bonds in an unusual intramolecular PCET process, wherein the electron travels to a proximal radical cation in concert with proton transfer to a weak Br?nsted base. Effective bond strength considerations are shown to accurately forecast the feasibility of alkoxy radical generation with a given oxidant/base pair.
A Highly Stereoselective Synthesis of Trans-1,2-Disubstituted Cycloalkanols
Cannone, P.,Bernatchez, M.
, p. 4025 - 4031 (2007/10/02)
The study of the reactions of 1,4-bis(bromomagnesio)pentane, 1,1-bis(bromomagnesio)hexane, 1,4-bis(bromomagnesio)heptane, and 1,4-bis(bromomagnesio)octane with aliphatic and aromatic carboxylic acid esters in tetrahydrofuran solution was undertaken in order to ascertain which factors influence isomer distribution.The yields of this annelation processes are in the range of 68-88percent.The formation of trans OH 1,2-disubstituted cyclopentanols having the alkyl groups cis is generally observed with yields of 77-96percent.The reaction of 1,5-bis(bromomagnesio)hexane with carboxylicacid esters is less stereoselective and is more influenced by steric effects.
Reaction of 1,4-Bis(bromomagnesio)pentane and 1,5-Bis(bromomagnesio)hexane with Carboxylic acid Esters. A Useful, Highly Stereoselective Annelation
Canonne, P.,Bernatchez, M.
, p. 2147 - 2148 (2007/10/02)
1,4-Bis(bromomagnesio)pentane and 1,5-bis(bromomagnesio)hexane have been prepared in THF solution, when treated with carboxylic acid esters, they afford trans diastereomeric bisubstituted cycloalkanols via a highly diastereoselective intramolecular Grignard reaction.
