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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
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
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