New Synthesis and Hydroboration of Vinylphosphonates

Article abstract of DOI:10.1246/bcsj.53.1625

The Arbuzov reaction of trimethyl and triethyl phosphites with acyl chlorides gave 1-oxoalkylphosphonates in 57-80percent yields.The Wittig reaction of the phosphonates with methylenetriphenylphosphorane gave vinylphosphonates in 25-59percent yields.Hydroboration of vinylphosphonates in oxolane gave 2-hydroxyethylphosphonates in 50-65percent yields.The procedure seems to be a good synthetic method to afford 1-alkyl-substituted 2-hydroxyethylphosphonates which have one more carbon atom than the starting 1-oxoalkylphosphonates.