51250-37-4Relevant academic research and scientific papers
Anomeric-like Substituent Effects on the Chair-Chair Conformational Equilibrium of the 2-Oxo-1,3,2-oxazaphosphorinane Ring System
Bentrude, Wesley G.,Setzer, William N.,Khan, Mamunur,Sopchik, Alan E.,Ramli, Emmanuel
, p. 6127 - 6131 (1991)
The chair-chair equilibria for a series of 5,5-dimethyl-2-oxo-(2-p-X-anilino)-1,3,2-oxazaphosphorinanes were determined by 1H NMR. The percentage of chair conformer with the p-X-anilino group axial is increased by the presence of electron withdrawing X, while the opposite is true for electron-donor para X.Reasonably good linear plots of log K vs ? were obtained in the solvents acetone-d6, CD3CN, and CD3NO2 with ρ = 0.28-0.36.These results are interpreted in terms of the dominance of the endo anomeric effect involving overlap of the endocyclic N(3) and O(1) p lone pairs with the axial P-N ?* orbital (p-XC6H4NHP).
Highly Regio- And Diastereoselective Tethered Aza-Wacker Cyclizations of Alkenyl Phosphoramidates
Mague, Joel T.,Sathyamoorthi, Shyam,Shinde, Anand H.,Thomas, Annu Anna
supporting information, p. 14732 - 14758 (2021/11/12)
We present highly diastereoselective tethered aza-Wacker cyclization reactions of alkenyl phosphoramidates. "Arming"the phosphoramidate tether with 5-chloro-8-quinolinol was essential to achieving >20:1 diastereoselectivity in these reactions. The substrate scope with respect to alkenyl alcohols and phosphoramidate tether was extensively explored. The scalability of the oxidative cyclization was demonstrated, and the product cyclophosphoramidates were shown to be valuable synthons, including for tether removal. With chiral alkenyl precursors, enantiopure cyclic phosphoramidates were formed.
Spectroscopic characterization and ab initio calculations of new diazaphosphole and diazaphosphorinane
Afshar,Shariatinia,Zare,Ghaziany
experimental part, p. 287 - 294 (2012/06/01)
Phosphoryl chloride is used as a starting material to synthesize new diazaphosphole, 4-OCH3-C6H4NHP(O)[4-CH 3-NH-C6H3-NH] (1) and diazaphosphorinane, 4-OCH3-C6H4
