Isolable 1,2‐Oxaphosphetanes: From Curiosities to Starting Materials for the Synthesis of Olefins

Lopez‐Ortiz, Fernando; López, Jesús García; Manzaneda, R. A.; Alvarez, Isidro J. Perez

doi:10.1002/chin.200452249

Cited by 2 publications

(2 citation statements)

References 1 publication

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Thus, 2-chloro-1,2λ 5 -oxaphosphetanes as a result of [1,3]-migration of chlorine atom to carbon atom underwent 2-chlorooxaphosphetane-2-chlorooxyphosphine oxide rearrangement to convert into the 2-chlorooxyphosphine oxides 35. Thermal stability of 2-chloro-1,2λ 5 -oxaphosphetanes was decreased in case of oxaphosphetanes which not contain at С4 atom strong acceptor substituents, which rearranged into chloroalkylphosphonates at room temperature (Table 3).…”

Section: Properties Of Oxaphosphetanesmentioning

confidence: 99%

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

Kolodiazhna

Kolodiazhnyi

2016

Preprint

View full text Add to dashboard Cite

Abstract:Results of research into four-membered 2-halo-1,2λ 5 -oxaphosphetane phosphorus(V)-heterocycles are presented. The preparation of 2-halo-1,2λ 5 -oxaphosphetanes by reaction of Phaloylides 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-1,2λ 5 -oxaphosphetanes were isolated as individual compounds and their structures were confirmed by 1 Н-, 13 C-, 19 F-and 31 Р-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-1,2λ 5 -oxaphosphetanes are reviewed. The 2-chloro-1,2λ 5 -oxaphosphetanes, rearrange with formation of 2-chloroalkylphosphonates or convert into trans-phosphorylated alkenes depending on the substituents at the α-carbon atom. Prospective synthetic applications of 2-halo-1,2λ 5 -oxaphosphetanes are analyzed. The 2-halo-1,2λ 5 -oxaphosphetanes may be easily converted to various alkenylphosphonates: allylor vinylphosphonates, phosphorus ketenes, thioketenes, ketenimines.

show abstract

Section: Properties Of Oxaphosphetanesmentioning

confidence: 99%

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

Kolodiazhna

Kolodiazhnyi

2016

Preprint

View full text Add to dashboard Cite

show abstract

“…2-Chloro-1,2λ 5 -oxaphosphetanes enter into a number of interesting chemical conversions. Thus, 2-chloro-1,2λ 5 -oxaphosphetanes as a result of [1,3]-migration of chlorine atom to carbon atom underwent 2-chlorooxaphosphetane-2-chlorooxyphosphine oxide rearrangement to convert into the 2-chlorooxyphosphine oxides 35. Table 3.…”

Section: Properties Of Oxaphosphetanesmentioning

confidence: 99%

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

Kolodiazhna¹,

Kolodiazhnyi²

2016

Preprint

View full text Add to dashboard Cite

Abstract:Results of research into four-membered 2-halo-1,2λ 5 -oxaphosphetane phosphorus(V)-heterocycles are presented. The preparation of 2-halo-1,2λ 5 -oxaphosphetanes by reaction of Phaloylides 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-1,2λ 5 -oxaphosphetanes were isolated as individual compounds and their structures were confirmed by 1 Н-, 13 C-, 19 F-and 31 Р-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-halon-1,2λ 5 -oxaphosphetanes are reviewed. The 2-chloro-1,2λ 5 -oxaphosphetanes, rearrange with formation of 2-chloroalkylphosphonates or convert into trans-phosphorylated alkenes depending on the substituents at the α-carbon atom. Prospective synthetic applications of 2-halo-1,2λ 5 -oxaphosphetanes are analyzed. The 2-halo-1,2λ 5 -oxaphosphetanes may be easily converted to various alkenylphosphonates: allyl-or vinylphosphonates, phosphorus ketenes, thioketenes, ketenimines.

show abstract

Isolable 1,2‐Oxaphosphetanes: From Curiosities to Starting Materials for the Synthesis of Olefins

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 2 publications

References 1 publication

Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ<sup>5</sup>-oxaphosphetanes

Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ<sup>5</sup>-oxaphosphetanes

Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ<sup>5</sup>-oxaphosphetanes

Contact Info

Product

Resources

About

Isolable 1,2‐Oxaphosphetanes: From Curiosities to Starting Materials for the Synthesis of Olefins

Abstract: For Abstract see ChemInform Abstract in Full Text.

Cited by 2 publications

References 1 publication

Synthesis, Properties and Stereochemistry of 2-Halo-1,2&lambda;<sup>5</sup>-oxaphosphetanes

Synthesis, Properties and Stereochemistry of 2-Halo-1,2&lambda;<sup>5</sup>-oxaphosphetanes

Synthesis, Properties and Stereochemistry of 2-Halo-1,2&lambda;<sup>5</sup>-oxaphosphetanes

Contact Info

Product

Resources

About

Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ<sup>5</sup>-oxaphosphetanes

Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ<sup>5</sup>-oxaphosphetanes

Synthesis, Properties and Stereochemistry of 2-Halo-1,2λ<sup>5</sup>-oxaphosphetanes