{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,2,28]],"date-time":"2026-02-28T04:28:44Z","timestamp":1772252924441,"version":"3.50.1"},"reference-count":48,"publisher":"MDPI AG","issue":"10","license":[{"start":{"date-parts":[[2016,10,17]],"date-time":"2016-10-17T00:00:00Z","timestamp":1476662400000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>Results of research into four-membered 2-halo-1,2\u03bb5-oxaphosphetane phosphorus(V)-heterocycles are presented. The preparation of 2-halo-1,2\u03bb5-oxaphosphetanes by reaction of P-haloylides with carbonyl compounds is described. The mechanism of asynchronous [2+2]-\u0441ycloaddition of ylides to aldehydes was proposed on the base of low-temperature NMR investigations. 2-Halo-1,2\u03bb5-oxaphosphetanes were isolated as individual compounds and their structures were confirmed by 1\u041d-, 13C-, 19F- and 31\u0420-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-1,2\u03bb5-oxaphosphetanes are reviewed. The 2-chloro-1,2\u03bb5-oxaphosphetanes, rearrange with formation of 2-chloroalkyl-phosphonates or convert into trans-phosphorylated alkenes depending on the substituents at the \u03b1-carbon atom. Prospective synthetic applications of 2-halo-1,2\u03bb5-oxaphosphetanes are analyzed. The 2-halo-1,2\u03bb5-oxaphosphetanes may be easily converted to various alkenylphosphonates: allyl- or vinylphosphonates, phosphorus ketenes, thioketenes, ketenimines.<\/jats:p>","DOI":"10.3390\/molecules21101371","type":"journal-article","created":{"date-parts":[[2016,10,17]],"date-time":"2016-10-17T10:33:16Z","timestamp":1476700396000},"page":"1371","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":4,"title":["Synthesis, Properties and Stereochemistry of 2-Halo-1,2\u03bb5-oxaphosphetanes"],"prefix":"10.3390","volume":"21","author":[{"given":"Anastasy","family":"Kolodiazhna","sequence":"first","affiliation":[{"name":"Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1, Murmanska Street, Kiev 02094, Ukraine"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Oleg","family":"Kolodiazhnyi","sequence":"additional","affiliation":[{"name":"Institute of Bioorganic Chemistry and Petrochemistry, National Academy of Sciences of Ukraine, 1, Murmanska Street, Kiev 02094, Ukraine"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2016,10,17]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"65","DOI":"10.2174\/1570193043488962","article-title":"Isolable 1,2-Oxaphosphetanes: From curiosities to starting materials for the synthesis of olefins","volume":"1","year":"2004","journal-title":"Mini-Rev. 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