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Issue 12, 2019
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Synthesis and characterization of a pair of O-fac/O-mer 12-P-6 alkyloxaphosphates with a P–O–C–C four-membered ring

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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

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Article information


Submitted
19 Nov 2018
Accepted
15 Feb 2019
First published
19 Feb 2019

This article is Open Access
All publication charges for this article have been paid for by the Royal Society of Chemistry

Chem. Sci., 2019,10, 3466-3472
Article type
Edge Article

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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