From Phosphonic Acid to O–P Heterocycles Using MW: An Access to [5]-, [6]- and [8]-Membered Annelated Phosphinates
Résumé
In this work, we describe the synthesis of O,P-heterocycles with sizes of 5, 6 and 8 atoms. A one pot-two steps processes accounts for the preparation of 1,2-oxaphosphinane and 1,2-oxaphosphacane. The synthesis of 1,2-oxaphospholane requires two steps involving the installation of functional group on the phosphinate introducing a P-O bond followed by the formation of a Pd-catalyzed C-P bond formation. Their molecular structures were assessed by single crystal X-ray diffraction. The geometries of the studied compounds were optimized using density functional theory (DFT) at the B3LYP and M06-2X hybrid functionals and compared to the experimental solid state data. In addition, Hirchfeld surfaces and frontier molecular orbitals were described.