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

نویسندگان

  • Anastasy O Kolodiazhna
  • Oleg I Kolodiazhnyi
چکیده

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.

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

منابع مشابه

Synthesis and Spectral Studies on Thorium (IV) Coordination Compounds of 4-[N-(2-Hydroxybenzalidene)amino] AntipyrineSmeicarbazone and 4-[N-Cinnamalidene) amino] ANtipyrine Semicarbazone

The stereochemistry of the actinide elements has recently undergone considerable development and a wide variety of coordination numbers and geometries have been observed. This structural versatility arises from the lack of strong crystal field effects for the 5f-electronic configurations as well as from the large ionic radii of these metal ions, which change markedly with oxidation number, ...

متن کامل

Synthesis of 4-(2-Methylthiazol-4-yl)-Hexahydroquinoline and 1,4-Dihydropyrimidin Derivatives

A series of new hexahydroquinoline and 1,4-dihydropyrimidine derivatives were synthesized. Condensation of 2-methyl- thiazole-4-carboxaldehyde (1) with 1,3-cyclohexanedione and alkyl 3- aminocrotonate afforded 4-(2-methyl-thiazol-4-yl)-hexahydroquinoline while condensation of aldehyde (1) with benzoyl acetone and thiourea gave 1,4-dihydropyrimidine derivatives. The stereochemistry of 1,4-dihydr...

متن کامل

One pot three-component synthesis of imidazole derivatives using NH3/NH4Cl

Imidazole is a planar, five membered heteroaromatic molecule with pyrrole type and pyridine type annular nitrogens. Several approaches are available of imidazoles from alpha halo ketones, aminonitrile, aldehyde ect. Reactivity of imidazole and benzimidazole is referred from sets of  resonance structure in which the dipolar contributors have finite importance. Imidazoles among the principal grou...

متن کامل

Total Synthesis and Stereochemistry of ( + ) - Phyllanthocindiol 843 Paul

The crude ethanol extract obtained from the root of Phyllanthus acuminatus Vahl was found to inhibit growth in the P388 leukemia system in mice. Kupchan and coworkers traced the significant pharmacological properties to a bisabolane sesquiterpene glycoside, (+)-phyllanthoside (0' Although the structure of the corresponding aglycon (+)-phyllanthocin (2) was elucidated by single-crystal X-ray dif...

متن کامل

ذخیره در منابع من


  با ذخیره ی این منبع در منابع من، دسترسی به آن را برای استفاده های بعدی آسان تر کنید

برای دانلود متن کامل این مقاله و بیش از 32 میلیون مقاله دیگر ابتدا ثبت نام کنید

ثبت نام

اگر عضو سایت هستید لطفا وارد حساب کاربری خود شوید

عنوان ژورنال:
  • Molecules

دوره 21 10  شماره 

صفحات  -

تاریخ انتشار 2016