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Molecules 2016, 21(10), 1371; doi:10.3390/molecules21101371

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
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Author to whom correspondence should be addressed.
Academic Editors: György Keglevich and Derek J. McPhee
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)

Abstract

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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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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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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