14609-90-6

Upstream product

• 3426-89-9 phenyl phosphorodichloridite 
• 683-60-3 sodium isopropylate 
• 67-63-0 isopropyl alcohol 
• 180906-75-6 C₁₁H₁₅O₄P 
• 54921-72-1 phenyl H-phosphonate ammonium salt 
• 4712-55-4 diphenyl hydrogen phosphite 

Relevant academic research and scientific papers

New and one pot chemoselective synthesis of nucleoside 5′-H- phosphonate diesters

Arbuzov reaction of phenyl phosphorodichloridite with two equiv of alcohol, or mixture of one equiv of alcohol and one equiv of tert-butyl alcohol, led to the corresponding aryl H-phosphonate diesters. Following displacement of the H-phosphonate diesters

Studies on aryl H-phosphonates. 3. Mechanistic investigations related to the disproportionation of diphenyl H-phosphonate under anhydrous basic conditions

Diphenyl H-phosphonate undergoes under anhydrous reaction conditions a base-promoted disproportionation to triphenyl phosphite and phenyl H- phosphonate. On the basis of 31P NMR data the most likely mechanism for this transformation was proposed. In order to substantiate these findings and to get a deeper insight into the chemistry of aryl H-phosphonate esters, we carried out also some studies on activation of phenyl and diphenyl H- phosphonates with various condensing agents. We found that aryl vs alkyl esters of phosphonic acid often follow different reaction pathways during the activation, and this can most likely be traced back to higher electrophilicity of the phosphorus centre and to higher reactivity of the P- H bonds in aryl H-phosphonate derivatives.