Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ5-oxaphosphetanes
AbstractResults 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
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Kolodiazhna, A.O.; Kolodiazhnyi, O.I. Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ5-oxaphosphetanes. Molecules 2016, 21, 1371.
Kolodiazhna AO, Kolodiazhnyi OI. Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ5-oxaphosphetanes. Molecules. 2016; 21(10):1371.Chicago/Turabian Style
Kolodiazhna, Anastasy O.; Kolodiazhnyi, Oleg I. 2016. "Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ5-oxaphosphetanes." Molecules 21, no. 10: 1371.
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