Sciencemadness Discussion Board

lithium phenylacetylide

Sadia Noor - 10-3-2016 at 19:43

Please somebody give me method for the Preparation of Lithium Phenylacetylide

clearly_not_atara - 11-3-2016 at 11:34

Quote: Originally posted by Sadia Noor  
Please somebody give me method for the Preparation of Lithium Phenylacetylide

See the preparation in the Prepublication forum:

http://www.sciencemadness.org/talk/viewthread.php?tid=18681

It's always a good idea to check prepub for the compund you're looking for or a similar one before asking here. Be aware that phenylacetylene is not a precursor for the title compound.

Quote:
what would happen if instead of formic acid, formamide was used along with a reducing agent like NaBH3CN or the formamide was itself used to do a one pot reduction of the enamine formed ?


It's not quite the same thing but I always thought the direct thermal conversion of allenes to nitrones was pretty cool:

http://pubs.acs.org/doi/suppl/10.1021/ol900292r

I searched for formamide and didn't find much; it seems like hydroamination using simple amines is more common, although interestingly alpha-phenylethylformamides undergo an annulation with alkynes:

http://pubs.acs.org/doi/abs/10.1021/ja1102037

CuReUS - 12-3-2016 at 05:10

Quote: Originally posted by clearly_not_atara  
Be aware that phenylacetylene is not a precursor for the title compound.

why not ? won't reacting phenylacetylene with LDA or BuLi or even LiNH2 give lithium phenylacetylenide ?
http://www.orgsyn.org/demo.aspx?prep=CV8P0391

Quote:
I searched for formamide and didn't find much;

as I always like to believe and say,just because it hasn't been done before doesn't make it impossible.If someone told me that you could make ketones from alkynes using only formic acid acid, i wouldn't have believed them.But its true.
Quote:
it seems like hydroamination using simple amines is more common

but most of them if not all ,need a catalyst.

clearly_not_atara - 12-3-2016 at 14:03

By "title compound" I meant phenylacetylcarbinol, not lithium phenylacetylide. Sorry for the misunderstanding.