319488-97-6Relevant articles and documents
Synthesis of Pentacoordinated Spiro[44]phosphoranes by Reaction of Cyclic Phosphazenyl Anions with Epoxides: Study of their P-Remote Functionalization and Hydrolysis
Sansores Peraza, Pablo M.,García López, Jesús,Navarro, Yolanda,Iglesias, María J.,López Ortiz, Fernando
, p. 600 - 616 (2021/11/16)
The synthesis of a new family of pentacoordinated spiro[4.4]phosphoranes stabilized by the ortho-benzamide bidentate ligand (oBA, -C6H4-2-C(O)NH-) through reaction of C,Cortho-dilithiated phosphazenes with oxiranes is reported. Mixtures of epimers that differ in configuration at the phosphorus atom were obtained with moderate to high yields and diastereoselectivities. C3-Disubstituted derivatives could be separated, which provided access to enantiopure products arising from the reaction with (R)-2-phenyloxirane. Stereomutation was observed by heating the spirophosphoranes at 100 C. Directed ortholithiation of spirophoshoranes followed by electrophilic quench reactions including carbon-based and heteroatom-based electrophiles afforded derivatives functionalized in a remote position with respect to the phosphorus atom. Benzoic acid catalyzed hydrolysis of spirophosphoranes furnished ortho-(γ-hydroxyalkylphosphoryl)benzamides by cleavage of the P O and P N bonds with retention of the phosphorus configuration. In contrast, alkaline hydrolysis led to the formation of γ- hydroxyphosphinic acids and benzamide.
Olefination reactions through phosphazenes
Perez,Ortiz
, p. 2029 - 2030 (2007/10/03)
The first synthesis of di-, tri- and tetrasubstituted alkenes through reaction of lithium P-diphenyl(alkyl)(N-carboxymethyl)phosphazenes with aldehydes and ketones is reported.