Rattata2 - 22-6-2009 at 23:30
Eh, forgot to change the pass on my other account and lost the email :p
Anyways, I understand that ketones will react with hydrazine and substituted hydrazines to form a hydrazone, and that this can be subsequently reduced
to an alkane.
My question is whether an alpha-keto acid (such as pyruvic acid) would react with a hydrazine-containing compound as well forming the hydrazone
intermediate, or would the carboxylic acid group would get in the way and cause some kind of side-reaction or whatever?
Rattata2 - 23-6-2009 at 14:44
Nothing? Jeez it can't be that hard of a question
I'm essentially asking if the acid group of a keto-acid would react with hydrazine in a Wolff-Kishner reduction if it were attempted...or if it would
be left alone and just the ketone group attacked (or neither.)
entropy51 - 23-6-2009 at 14:58
Rattata, Nicodem will probably once again expose my ignorance of electron pushing, but if I understand your question, these guys used a Wolff-Kishner
reduction for pyruvate to propionate. Apparently the carboxyl group wasn't too bothered by everything going on around it. Is that what you're
asking?
http://pubs.acs.org/doi/abs/10.1021/ja01155a546
[Edit] Thanks to Ozone for providing the article below. I guess he understood your question in the same way I did.
[Edited on 23-6-2009 by entropy51]
Ozone - 23-6-2009 at 15:21
Patience....
Is over-rated.
Searching the literature is not.
Cheers,
O3
Attachment: Mosbach 1951 JACS 73-11-5477 Wolff-Kishner Redcution of Pyruvic and 3-formylpropionic acids.pdf (276kB)
This file has been downloaded 653 times
Rattata2 - 23-6-2009 at 15:43
Nice 
Yes that's what I was asking, and I do believe that answers my question
pretty well! Good find, I had trouble finding anything on this topic at all...
Guess the only way to really know what kinds of yields to expect with this though is to try it. Unfortunately I can't think of any keto-acids I have
on-hand and I don't have any hydrazine atm either :p One day I'll try it tho.
Any other comments on this?
entropy51 - 23-6-2009 at 15:52
My comment is why didn't you search just like we did?
Rattata2 - 23-6-2009 at 16:05
Eh idk why I didn't search the pubs, I tried to find it on google and didn't come up with much at all.
I will next time, appreciate you guys helping
entropy51 - 23-6-2009 at 16:34
I call BS. I searched on Google and that abstract came right up. Shame on you! But I guess it's OK. For once. But be careful of Necrosyrtes
chemicus or you'll be in a world of hurtin'.