Alyx Woodward (obsolete) @Alyx@computerfairi.es

Chara's right

we're alone in this, whatever it is

there ain't nobody coming to help us

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

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

reading articles about alloy chemistry make my head hurt

bleh, lying down and dozing off to 2nd season MLP:FIM

oh huh another Jupiter impact

https://www.skyandtelescope.com/astronomy-blogs/explore-night-bob-king/texas-amateur-detects-possible-impact-on-jupiter/

bleh. real unhappy this morning

and finally water gets eliminated and you get the allene. or something like that. I'm trying to do that in my head instead of writing it down (it's good practice for me!)

well, fun! the _Organic Syntheses_ article then goes on to show a whole bunch of reactions that allenylcarbinol has been used in.

one to file away for who-knows-when.

synthesis involves refluxing propargyl alcohol, HC≡C-CH₂OH, with paraformaldehyde (that's the insoluble polymeric form of formaldehyde, much nicer to handle than formalin), diisopropylamine, copper(I) iodide as a catalyst, in tetrahydrofuran. well!

presumably the diisopropylamine is a sufficiently strong base to strip the acetylenic hydrogen on the propargyl alcohol, which then coordinates with the copper(I). then this acetylide attacks formaldehyde (formed in situ from the paraformaldehyde)

oh uh lemme do _Organic Syntheses_ roulette again

(among other things it's kinda calming)

and the number is 4263!

http://orgsyn.org/demo.aspx?prep=v94p0153

wow, ok...a curious reaction, synthesis of something that looks like a valuable synthetic intermediate even though it's only a few carbons long, allenylcarbinol. so H₂C=C=CH-CH₂OH. a more systematic name is 2,3-butadienol.

allenes are funny creatures!