36912-27-3Relevant academic research and scientific papers
Acid-Catalyzed Solvolysis of Highly Reactive Phosphoramidates: A Stereochemical Study
Wadsworth, William S.
, p. 1748 - 1753 (1987)
Two 2-substituted-5-(chloromethyl)-1,3,2-dioxaphosphorinanes have been prepared in which the 2-substituent is either imidazole or benzimidazole.The two phosphoramidates in which the 2-substituent is axial have opposite configurations as determined by NMR and solvolysis studies.Acid-catalyzed methanolysis in both cases is extremely rapid and proceeds by 100percent inversion.However, with weak nucleophiles or a nucleophile kept in low concentration, an intermediate is formed which has enough lifetime to allow at least partial equilibration about the phosphorus atom.Although a completely free phosphacylium ion is unlikely, with aromatic solvents a similar product ratio from both isomers which may reflect a common intermediate is approached.
Phosphorochloridates from phosphorohydrazides with ButOCl: Stereospecificity, selectivity and phosphorylium ion intermediates
Harger, Martin J.P
, p. 6749 - 6752 (2007/10/03)
The efficiency with which a six-membered cyclic phosphorochloridate can be obtained from the corresponding hydrazide with retention of configuration at phosphorus, using tert-butyl hypochlorite in tert-butyl alcohol, depends on how stereoelectronic factors influence the fate of an intermediate chloride-phosphorylium ion pair.
Silicon Phosphorus Analogies. Fluoride Activation of Nucleophilic Displacement at the Tetrahedral Phosphorus: An Example of Nucleophilic Assistance to Nucleophilic Substitution. 3
Corriu, Robert J. P.,Dutheil, Jean-Pierre,Lanneau, Gerard F.
, p. 1060 - 1065 (2007/10/02)
We report a mechanistic study of the activation of alcoholysis of the P-X bond (X= Cl, F) by F(1-).Cis and trans isomers of 2-halogeno-5-(chloromethyl)-5-methyl-2-oxo-1,3,2-dioxaphosphorinanes, 1 and 2, or their 2-thio analogues, 3 and 4, and epimeric 2-h
A Cyclic Phosphate: Base and Metal Acetate Catalyzed Ring Opening
Wadsworth, William G.,Wadsworth, William S.
, p. 1631 - 1637 (2007/10/02)
Six-membered ring phosphates in which a good leaving group is absent undergo methanolysis to give acyclic products that can reclose to the original cyclic system.Under basic conditions the sequence is not stereospecific, which is explained by assuming an
