137944-25-3Relevant articles and documents
A New Reagent for the Determination of the Optical Purity of Primary, Secondary, and Tertiary Chiral Alcohols and of Thiols
Alexakis, Alexandre,Mutti, Stephane,Mangeney, Pierre
, p. 1231 - 1237 (2007/10/02)
A new reagent is described for the determination of the enantiomeric excess of chiral alcohols.The derivatizing agent (22) is a diazaphospholidine, easily prepared from hexamethylphosphorous triamide (HMPT) and a chiral diamine having a C2 axis of symmetry: (R,R)-N,N'-dimethylcyclohexane-1,2-diamine.A large array of primary, secondary, and tertiary alcohols, functionalized or not, as well as thiols were successfully tested.The derivatization is fast at room temperature, proceeds without kinetic discrimination, does not need any added cosolvent or coreagent, andmay be run directly in an NMR tube.This new reagent allows an accurate analysis by 31P NMR spectroscopy, and after conversion of the trivalent phosphorus derivative to the corresponding P-sulfide in the NMR tube, a new 31P NMR spectrum may be recorded.In addition, most of the P-sulfide derivatives when submitted to GC or HPLC analyses exhibit base line separation.