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Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ5-oxaphosphetanes

Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1, Murmanska Street, Kiev 02094, Ukraine
Author to whom correspondence should be addressed.
Academic Editors: György Keglevich and Derek J. McPhee
Molecules 2016, 21(10), 1371;
Received: 31 August 2016 / Revised: 28 September 2016 / Accepted: 8 October 2016 / Published: 17 October 2016
(This article belongs to the Special Issue Recent Advances in Organophosphorus Chemistry)
Results of research into four-membered 2-halo-1,2λ5-oxaphosphetane phosphorus(V)-heterocycles are presented. The preparation of 2-halo-1,2λ5-oxaphosphetanes by reaction of P-haloylides with carbonyl compounds is described. The mechanism of asynchronous [2+2]-сycloaddition of ylides to aldehydes was proposed on the base of low-temperature NMR investigations. 2-Halo-1,2λ5-oxaphosphetanes were isolated as individual compounds and their structures were confirmed by 1Н-, 13C-, 19F- and 31Р-NMR spectra. These compounds are convenient reagents for preparing of various organic and organophosphorus compounds hardly available by other methods. Chemical and physical properties of the 2-halo-1,2λ5-oxaphosphetanes are reviewed. The 2-chloro-1,2λ5-oxaphosphetanes, rearrange with formation of 2-chloroalkyl-phosphonates or convert into trans-phosphorylated alkenes depending on the substituents at the α-carbon atom. Prospective synthetic applications of 2-halo-1,2λ5-oxaphosphetanes are analyzed. The 2-halo-1,2λ5-oxaphosphetanes may be easily converted to various alkenylphosphonates: allyl- or vinylphosphonates, phosphorus ketenes, thioketenes, ketenimines. View Full-Text
Keywords: 2-halo-1,2λ5-oxaphosphetanes; allylphosphonates; vinylphosphonates; phosphorus ketenes 2-halo-1,2λ5-oxaphosphetanes; allylphosphonates; vinylphosphonates; phosphorus ketenes
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MDPI and ACS Style

Kolodiazhna, A.O.; Kolodiazhnyi, O.I. Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ5-oxaphosphetanes. Molecules 2016, 21, 1371.

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