22894-35-5

Upstream product

• 705-60-2 (2-nitroprop-1-enyl)benzene 
• 29800-93-9 diethyl phosphite 
• 3893-35-4 1-diazo-1-phenyl-2-propanone 
• 762-04-9 phosphonic acid diethyl ester 
• 1067-71-6 Diethyl (2-oxopropyl)phosphonate 
• 591-50-4 iodobenzene 
• 38654-91-0 2-(diethoxyphosphino)-2-phenylacetic acid 
• 1080-32-6 O,O-diethyl benzylphosphonate 
• 53615-31-9 (Chlorocarbonyl-phenyl-methyl)-phosphonic acid diethyl ester 
• 917-54-4 methyllithium 
• 61997-67-9 2-benzenesulfonyl-2-methyl-3-phenyl-oxirane 

Downstream Products

• 74152-49-1 diethyl methyl-1 phenyl-2 ethenyl-1,2 phosphonate 
• 103-79-7 1-phenyl-acetone 
• 1080-32-6 O,O-diethyl benzylphosphonate 

Relevant academic research and scientific papers

Synthesis of α-arylphosphonates using copper-catalyzed α-arylation and deacylative α-arylation of β-ketophosphonates

Efficient methods for the direct arylation and deacylative arylation of β-ketophosphonates with iodoarenes in presence of a copper(I) or a copper(II) salt as the catalysts have been developed. The corresponding α-arylphosphonates were obtained in high yields. A tentative mechanism for the deacylative arylation reaction was proposed on the basis of the experimental data. Copyright

A general and efficient synthesis of β-ketophosphonates

The acylation of organocuprates or organolithiated reagents with 2-dialkylphosphonoalkanoyl chlorides or dialkylphosphonofluoroacetyl chlorides represents a general and efficient route to β-ketophosphonates.A Horner reaction between the lithiated anions derived from α-fluoro-β-ketophosphonates and aldehydes leads to 2-fluoro-2-enones whereas the lithiated anions derived from γ-acetylenic-β-ketophosphonates afford enynones. β-ketophosphonate / 2-dialkylphosphonoalkanoyl chloride / dialkylphosphonofluoroacetyl chloride / 2-fluoro-2-enone / enynone

A new synthesis of β-keto phosphonate from aryl epoxysulfones and dialkyl hydrogen phosphite

Reaction of α-subtituted arylsulfonyl epoxide with diethyl phosphite sodium salt gave β-keto phosphonate in good yield.

A New Synthesis of 1-Aryl-2-oxoalkylphosphonates from Nitroalkenes and Diethyl Phosphite

Addition of diethyl phosphite to nitroalkenes affords α-phosphoryl nitronates which, on treatment with m-chloroperbenzoic acid, are converted into 1-aryl-2-oxoalkylphosphonates.

Reactions of Ethyl phosphites with β-Nitrostyrenes. The Role of Nitrosoalkenes as Intermediates

3-Phenyl-2-substituted-indoles are formed in high yields in the reaction of Ph2C=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150 deg C while reaction with (EtO)2PO(1-)/(Et2O)P(O)H at room temperature forms the aziridines 1 with R = H, Me, Ph. 2,2-Diphenyl-3-substituted-2H-azirines formed by deoxygenation of the Michael-type aducts are postulated as intermediates.Reactions of PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P at 150 deg C or (EtO)2PO(1-)/(EtO)2P(O)H at room temperature give products resulting from the addition of the phosphorus nucleophile at the benzylidene carbonatom.Evidence for the formation of cyclic structures with pentacoordinated phosphorus atoms is presented for the reaction of Ph2C=C(Me)NO2 with (EtO)2PO(1-)/(EtO)2P(O)H and for PhCH=C(R)NO2 (R = H, Me, Ph) with (EtO)3P.The Michael-type adducts PhCHCH(R)NO2 (R = Me, Ph) undergo reaction upon treatment with aqueous base at 80-100 deg C followed by acidification to yield the 3-(diethoxyphosphinyl)-2-R-N-hydroxyindoles. 4-(Diethoxyphosphinyl)-3-R-4H-1,2-benzoxazines (13, R = Me, Ph) are formed by reaction with 85percent H2SO4 of the adducts of PhCH=C(R)NO2 with (EtO)2PO(1-) (R = Me) or (EtO)3P (R = Ph).

A Facile and General, One-pot Synthesis of 2-Oxoalkane Phosphonates from Diethylphosphonocarboxylic Acid Chlorides and Organometallic Reagents

An efficient and general method for the preparation of 2-oxoalkane phosphonates 2 is described.Diethylphosphono-2-alkanoyl chlorides are used to introduce directly the 2-oxophosphonate 1-substituted synthons on Grignard or cuprate reagents.