Issue 12, 2019

Synthesis and characterization of a pair of O-fac/O-mer 12-P-6 alkyloxaphosphates with a P–O–C–C four-membered ring

Abstract

Structurally characterized hexacoordinate organophosphorus compounds remain rare due to their highly reactive nature and thermal instability. Herein we report the first synthesis of a pair of O-facial and O-meridional hexacoordinate oxaphosphates (5B and 5D) obtained from the O-apical and O-equatorial β-hydroxyalkylphosphoranes 3 and 4. This was achieved by using the bulky C2F5-groups on the ortho-substituted aryl backbone. Calculations of the relative energies of possible isomers indicate 5B and 5D are thermodynamic products. Although the mechanisms of their formation and the determining factor of stereo-selectivity are still unclear, their isolation and structure conformation contributes to a formulation of a viable strategy for diastereoselective synthesis of heteroleptic hexacoordinate organophosphates.

Graphical abstract: Synthesis and characterization of a pair of O-fac/O-mer 12-P-6 alkyloxaphosphates with a P–O–C–C four-membered ring

Supplementary files

Article information

Article type
Edge Article
Submitted
19 11 2018
Accepted
15 2 2019
First published
19 2 2019
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 3466-3472

Synthesis and characterization of a pair of O-fac/O-mer 12-P-6 alkyloxaphosphates with a P–O–C–C four-membered ring

X. Jiang, Y. Toya, S. Matsukawa, S. Kojima, J. O. C. Jimenez-Halla, R. Shang, M. Nakamoto and Y. Yamamoto, Chem. Sci., 2019, 10, 3466 DOI: 10.1039/C8SC05158E

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