synthesis, properties and stereochemistry of 2-halo-1,2λ5-oxaphosphetanes

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ID: 223103
2016
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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.
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kolodiazhna2016moleculessynthesis, Use this key to autocite in the manuscript while using SciMatic Manuscript Manager or Thesis Manager
Authors Anastasy O. Kolodiazhna, Oleg I. Kolodiazhnyi
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Journal Journal of ethnopharmacology
Year 2016
DOI
10.3390/molecules21101371
URL
http://www.mdpi.com/1420-3049/21/10/1371
Keywords
phosphorus ketenesorganic chemistry

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