roamingnome
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imine reactivity ( direct carbamylation)
This gives me hope for the proposal….
J. Chem. Soc., Perkin Trans. 1, 1995, 699 - 704
Oxidation of imines to oxaziridines catalysed by transition metal complexes using molecular oxygen as the terminal oxidant
Well information is scant, but for those interested in carbamides of amines leading to oxazolines. Why cant the imine some how just do it. Why get
involved in reduction techniques. The imine is formed rapidly with microwaves and elimination of formed water with absorbent will give even higher
yields then the Indian groups ethanol method leading to 40% yield….
Now pure Organic mechanisms is not my strong suit, I always barley passed my O chem. tests that is….
But it seems that when isocyanic acid attacks an amine group the carbon forms the bond to the N atom. OK
So under some reaction condition the imine can form a reactive single bonded species that “cross the fingers” would react directly with cyanate.
Even if you had to use cyangen bromide to avoid amine isolation it would be interesting. I like the idea of using HCNO gas myself…
I just don’t fully know or grasp the bond movements needed at this time… is this possible?
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[Edited on 24-5-2007 by roamingnome]
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jon
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I've never seen an example like what you propose here i don't think it will fly you can theoretically react guanidine with halohydrins to make
aminooxazolines. this will eliminate NH4Cl
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roamingnome
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well thanks
i know it is abit off the wall
and in a new days lite there seems to be a hydrogen dilema
but then i saw the double bonded nitrogen in the oxazoline ring
glancing back to the double bond of the imine
saying theres somthing fishy here
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jon
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I don't think you'll have enough energy to cause that to tautomerize there's no use reinventing the wheel unless you have the time and research
dollars to devote to it.
in the chem beritche article on the akabori reaction I noticed they used nitrobenzene as the solvent in the reactions and another paper I read says
that the nitro function is probably the best thing for stabilizing carbanions about twice as effective as acetonitrile I thought It had some
pertinence, so i thought mention it. the halohydrin route you do the Sn2 with guanidine and react with acid and this splits off NH4Cl I read about
that a long time ago can't remember where.
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roamingnome
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sure there are a few expiriments collecting cob webs....
KETIMINES - The Direct Reaction Between Ketimines and Aliphatic Isocyanates
http://www.bayermaterialsciencenafta.com/resources/index.cfm...
i got full text then the link died , but try to upload this...
Gif of primary Ketimine
http://content.answers.com/main/content/wp/en-commons/thumb/5/5d/75px-Imine-(primary)-skeletal.png
i think thats what were dealing with
so isocyante lets see... what pops up...
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It turns out that this esoteric paper will have bearing on the one pot synthesis of oxazoline heterocycle
http://www.quantchem.kuleuven.ac.be/minh/Articles/JPCA/jp951...
hydrogen gas + primary imine + cyanate + acidic medium + autoclave = polymerized goo ?
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Catalytic Activation of Imine Derivatives Using Novel Lewis Acids
http://wwwsoc.nii.ac.jp/ssocj/journal/english/1998/199805sum...
japan i know has the techniques...... to do it...
[Edited on 25-5-2007 by roamingnome]
[Edited on 25-5-2007 by roamingnome]
[Edited on 25-5-2007 by roamingnome]
[Edited on 28-5-2007 by roamingnome]
[Edited on 29-5-2007 by roamingnome]
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