Sciencemadness Discussion Board

diekmann ring closure

kyanite - 2-8-2004 at 01:25

Have any of you guys heard of this mechanism? I saw it in a colledge book once, but the pictured only showed a secondary amine, with the same chain on each side with carboxylgroups, and i think sodium ethoxide reacting to form a cyclohexane type structure...

Google kills my initiative with all those dam pdfs...:mad: plus, most either talk about pyridine type compunds being made from other rings. Any help would be appretiated :(

Marvin - 2-8-2004 at 08:29

The amine itself has essentially nothing to do with the reaction. Try looking at,

http://orgchem.chem.uconn.edu/namereact/dieckmann.html

and,

http://themerckindex.cambridgesoft.com/TheMerckIndex/NameRea...

As the Merk says, its an intramolecular claisen condensation. If you are after a mechanism, look up claisen.

Assume by pyridine compounds you mean fused to other rings (like a quinoline), rather than a seperate ring. This is a shame because I'm after a good way to make pyridine.

kyanite - 2-8-2004 at 09:02

:) Thats the one!, well, the second link to be exact, it looks exactly like the reaction i saw... Thank you, that cleared up some questions i had about this method

Yeah, alot of the pdfs had chemicals like that quinoline, but sorry, i dont think i saw a route to pyridine,
dam adobe acrobat with the stupid load errors...

incitatus - 18-1-2005 at 08:47

pyridines are normally made via a Hantsch synthesis