time for _Organic Syntheses_ roulette
the number to search for today is...3672
http://orgsyn.org/demo.aspx?prep=v92p0156
*winces* this one's not exactly exciting, or easy to get. the target is an N-phosphoryl ynamine, CH₃(CH₂)₅C≡CN(CH₂Ph)P(=O)(OEt)₂
why would you want this stuff? apparently these ynamine derivatives are good synthetic intermediates in 2+2 cycloadditions (so, a route to getting 4-membered rings)
I can barely bring myself to comment on this thing
ok, I'll try. benzylamine is phosphorylated by reaction with diethyl phosphite, (EtO)₂P(=O)H, and iodoform (iodoform??) in diethyl ether. presumably the iodoform acts as a mild oxidant or perhaps a source of molecular iodine _in situ_, achieving the formation of the N-P bond
then the phosphorylated amine is reacted with 1-bromo-1-octyne, obtained by bromination of 1-octyne with N-bromosuccinimide and silver nitrate as a catalyst
the alkynylation reaction is catalyzed by copper(II) sulfate in the presence of o-phenanthroline (a well known bidentate ligand for transition metals) and tripotassium phosphate. presumably the copper acetylide is an intermediate
welp, file that one away till "never", more than likely