The Phosphonate-Phosphate and Phosphate-Phosphonate Rearrangement and Their Applications V [1]. On the Reaction of s-Butyllithium/TMEDA with Symmetrical Trialkyl Phosphates

Article abstract of DOI:10.1007/BF00807567

1-(Tributylstannyl)hexanol ((±)-8) is phosphorylated to give phosphate (±)-9 which is then transmetallated. The organolithium intermediate (±)-10 isomerizes to α-hydroxyphosphonate (±)-12. Similar intermediates are also formed upon direct deprotonation of triethyl, tri-n-propyl, and tri-n-butyl phosphate, which subsequently rearrange to α-hydroxyphosphonates (±)-14a-c.