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.
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.