The phosphonate-phosphate and phosphate-phosphonate rearrangement and their applications .5. On the reaction of s-butyllithium/TMEDA with symmetrical trialkyl phosphates

摘要

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