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Phosphorus, Sulfur, and Silicon and the Related Elements Volume 190, 2015 - Issue 12: Robert Holmes Special Issue
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Original Articles

Synthesis and Properties of Four-Membered Phosphorus Heterocycles-2-Fluoro-1,2λ5-Oxaphosphetanes

Anastasia O. KolodiazhnaInstitute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Murmanska Street, Kiev, 02094, UkraineCorrespondence[email protected]
&
Oleg I. KolodiazhnyiInstitute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, Murmanska Street, Kiev, 02094, Ukraine
Pages 2232-2245 | Received 24 Mar 2015, Accepted 17 May 2015, Published online: 10 Dec 2015
 
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GRAPHICAL ABSTRACT

Abstract

The preparation of four-membered phosphorus(V)-heterocycles, 2-fluoro-1,2λ5-oxaphosphetanes, by reaction of P-fluoroylides with carbonyl compounds is described. The reaction is stereoselective and leads preferentially to the formation of threo-1,2λ5-oxaphosphetanes. Oxaphosphetanes were isolated as individual compounds and their structures were confirmed by 1Н, 13C, and 31Р NMR spectra. The fluoro-1,2λ5-oxaphosphetanes may be easily converted to various alkenylphosphonates: allyl- or vinylphosphonates. This reaction represents a good method for the preparation of phosphorylated alkenes.

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