18104-91-1

Upstream product

• 110-91-8 morpholine 
• 3277-27-8 diethyl benzoylphosphonate 
• 108-91-8 cyclohexylamine 
• 109-89-7 diethylamine 
• 109-73-9 N-butylamine 
• 98-86-2 acetophenone 
• 98-88-4 benzoyl chloride 
• 762-04-9 phosphonic acid diethyl ester 
• 53378-83-9 O,O-diethyl-α-tosyloxybenzylphosphonate 
• 2303-76-6 sodium diethyl phosphite 
• 100-52-7 benzaldehyde 
• 4961-94-8 1-(diethoxyphosphinoyl)-1-phenyl-2-azaprop-1-ene 
• 591-50-4 iodobenzene 
• 201230-82-2 carbon monoxide 

Downstream Products

• 1080-32-6 O,O-diethyl benzylphosphonate 

Relevant academic research and scientific papers

Reactions of diethyl mesyl- or tosyloxyphosphonates with diethyl phosphite and base: A method claimed to yield bisphosphonates

Reactions of diethyl mesyl- or tosyloxyphosphonates with sodium diethyl phosphite in THF lead to the corresponding phosphono phosphates. Reaction of the mesyloxy derivative with diethyl phosphite in pyridine gives the phosphono phosphate as minor product.

Single-step preparation of 1-hydroxybisphosphonates via addition of dialkyl phosphite potassium anions to acid chlorides

The addition reaction between the potassium anion of dialkyl phosphites and acid chlorides at low temperature produced tetraalkyl 1- hydroxybisphosphonates, whereas the corresponding lithium anion gave mostly the rearranged products tetraalkyl phosphono phosphates. The rate of rearrangement was found to be dramatically accelerated by the presence of bulky substituents at the α-position of the acid chloride. Intermediates arising from the addition of dibenzyl phosphite anion rearranged more readily than those obtained from diethyl phosphite anion, but again less so for the potassium anion reagent.

Tetraalkyl hydroxymethylene-bisphosphonate and dialkyl 1-diphenylphosphinoyl-1-hydroxy-ethylphosphonate derivatives by the pudovik reaction and their rearranged products

The reaction of diethyl α-oxoethylphosphonate and diethyl oxobenzylphosphonate with diethyl phosphite, dimethyl phosphite, and diphenylphosphine oxide affords, depending on the substrates and conditions (nature and quantity of the amine catalyst, temperat

Synthesis of acylphosphonates by a palladium-catalyzed phosphonocarbonylation reaction of aryl iodides with phosphites

Acylphosphonates are conveniently synthesized from aryl iodides by a palladium-catalyzed reaction with dialkyl phosphites under an atmospheric pressure of carbon monoxide. The reaction demonstrates the first example of the use of phosphorus nucleophiles in related metal-catalyzed carbonylation reactions.

Sigmatropic isomerizations in azaallyl systems: XX. N- Alkylbenzimidoylphosphonates

Synthetic approaches are developed to benzimidoylphosphoryl derivatives containing electronically and sterically diverse alkyl substituents on the nitrogen atom, as well as their prototropic isomers. Regularities in prototropic transitions in the phosphorylated C=N-C triad were revealed and applied in the synthesis of α-aminophosphonic acid derivatives. 2004 MAIK "Nauka/Interperiodica".

Lanthanoid-metal-mediated reaction of acylphosphonates: evidence for the formation of an acyllanthanoid complex

The reactions of diethyl acylphosphonates (1a-e) with Yb and Sm were examined.Reactivities of Yb to 1a-e are different from those of Li and Na.Typically, ethyl benzoylphosphonate (1a) reacts with Yb metal in tetrahydrofuran-hexamethylphosphoramide to afford diethyl 1,2-diphenyl-2-oxoethyl phosphate (2a) and diethyl 1-(diethyl-phosphoryloxy)-1-phenylmethylphosphonate (3a) The formations of 2a and 3a were explained best by the formation of acylytterbium complexes.Keywords: Ytterbium; Samarium; Acylphosphonate; Phosphorus

A NEW METHOD FOR ACYLATION OF ENOLATES BY MEANS OF DIALKYL ACYLPHOSPHONATES AS ACYLATING AGENTS

Acylations of various enolates by means of diethyl acylphosphonates were described.For the acylation of acetophenone, lithium bis(trimethylsilyl)amide (LSA) was found to be suitable as the base.The scope and limitation of the benzoylation using diethyl benzoylphosphonates were also described.

DIALKYL ACYLPHOSPHONATES: A NEW ACYLATING AGENT OF ALCOHOLS

Diethyl benzoylphosphonate (1) underwent facile benzoylation of alcohols in the presence of DBU.Reactions of diols containing primary and secondary hydroxyl groups with 1 gave predominantly monobenzoates in which primary hydroxyl groups were highly selectively benzoylated.Related acylations were also described.

Acylphosphonates: P-C Bond Cleavage of Dialkyl Acylphosphonates by Means of Amines. Substituent and Solvent Effects for Acylation of Amines

Studies on the benzoylation of amines of dialkyl benzoylphosphonates (1A-F) were described in detail. Stoichiometric reactions of diethyl benzoylphosphonate (1B) with a variety of amines (2a-i) gave amides as the main products along with diethyl phosphonate (4B) and α-(phosphoryloxy)benzyl phosphonate (5B). The yields of amides increased with the ratio of 1B/2a-i. The use of hindered dialkyl benzoylphosphonates resulted in high yields of amides while the reaction rates decreased markedly. The benzoylations of n-propylamine (2d) with 1B in various solvents having dielectric constants of 1.9-36.7 were conducted. The yields of N-n-propylbenzamide (3d) and 5B were surprisingly almost constant. However, the reaction rates varied as follows. In nonpolar solvents such as n-hexane and cyclohexane benzoylation was remarkably rapid while the benzoylation in methylene chloride was much slower than that in other solvents used. Compound 1B underwent smooth reaction with aliphatic amines but did not react with aromatic amines under the same conditions. Selective N-benzoylation of the bifunctional amine, ethanolamine, was achieved by means of diisopropyl benzoylphosphonate (1C) in tetrahydrofuran. The use of the hindered dialkyl benzoylphosphonate 1C resulted in poorer yields of amides in the case of the reaction with a hindered amine such as diethylamine, but higher yields of amides in the case of primary amines. Addition of triethylamine and 4-(dimethylamino)pyridine (DMAP) slightly accelerated the benzoylation, but yields of amides were similar to those in the absence of the catalysts. Optimum conditions for high yields of amides were proposed for the practical use of dialkyl benzoylphosphonates as the acylating agents in the present reaction.