Sciencemadness Discussion Board

Blog Syn

synthetic.madness - 21-2-2013 at 17:51

So I thought some members would be interested in this. In a world of systemic yield/ selectivity inflation and 32- step syntheses that will likely never be repeated, this blog is a welcome addition:

http://blog-syn.blogspot.ca/

Rich_Insane - 21-2-2013 at 18:29

Very interesting. There's a whole bunch of papers I can think of that have given me practically useless methods -- it's good to have a professional testing these things out!

Boffis - 28-2-2013 at 17:58

Yes very interesting! Its just how to offer these guys moral support to keep up the good work.

smaerd - 28-2-2013 at 19:14

Love the blog! Awesome idea.

Here's a reaction to debunk hehe:
Ali Khalafi-Nezhad, Abolfath Parhami, Mohammad Navid Soltani Rad
Efficient method for the direct preparation of amides from carboxylic acids using tosyl chloride under solvent-free conditions, Tetrahedron Letters, Volume 46, Issue 40, 3 October 2005, Pages 6879-6882, ISSN 0040-4039, 10.1016/j.tetlet.2005.08.021.
(http://www.sciencedirect.com/science/article/pii/S0040403905...)

Rich_Insane - 1-3-2013 at 11:33

I've got a couple of other papers concerning amide synthesis. They look way too good to be true. In fact, when I've tried them out, they don't work well at all -- one gives no yield and another gives ridiculously low yields, if anything. But since I am a noob chemist, I suspect that my technique is partially to blame.

Still, I'd like to know exactly how much of my failure is due to poor technique and how much is due to the paper itself.

Here is one particular reference describing one-pot synthesis of amides from aldehydes via oxime and copper sulfate:


Aldehyde to Amide

There are some others out there concerning the use of zinc salts for this rearrangement. For example: "Cost efficient synthesis of amides from oximes with indium or zinc catalysts"; Volume 51, Issue 20, 19 May 2010, Pages 2724–2726

Nicodem - 1-3-2013 at 11:37

It would be stupid to waste experimental time on Indian and Iranian articles like these, when their nature is obvious already by reading them. If anything, it is the type of articles like the ones they already checked that are of interest for the wider audience - articles from the the big and respectable groups.

paw_20 - 1-3-2013 at 12:42

I was about to look into that aldehyde to amide paper myself over the next couple weeks Rich_Insane, and try the analogous syntheses with indium and zinc salts. I also believe I saw one with nickel salts, but I can't find it at the moment. If synthetic.madness doesn't get around to it first, I'll post something.

Rich_Insane - 3-3-2013 at 22:09
Quote:

It would be stupid to waste experimental time on Indian and Iranian articles like these, when their nature is obvious already by reading them. If anything, it is the type of articles like the ones they already checked that are of interest for the wider audience - articles from the the big and respectable groups.


I've seen quite a few mentions of other transition metal catalysts as a means for rearranging oximes to amides. I wouldn't mention that reference otherwise, but I am curious to see if the paper is completely false.


paw_20: I've sent you a PM with the reference you seek. Would be good to see if this actually works.