Sciencemadness Discussion Board

Reductions of Nitro Compounds

chemaddict - 27-8-2013 at 02:28

Hi everyone

i am a studying reactions of nitro compounds and i found a couple differences in some references on this site to what i have been learning so far.
As we all no that the complete reduction of the nitro group proceeds through a number of intermediates , The references that i am asking about is the reduction with ammonium formate or (ammonium chloride with elemental zinc. It claims oximes can be reduced to amines.From what i have learn't so far this would stop at the hydroxyl amine stage .could someone clear this up for me and provide some mechanisms why this should be different to what i am understanding.
I no sodium in alcohol reduces oximes completely to amines but could i get some help understanding why the sodium reduction mechanism is different than most other dissolving metal mechanism


thanks in advance

chemaddict

<!-- bfesser_edit_tag -->[<a href="u2u.php?action=send&username=bfesser">bfesser</a>: un-capitalized subject]

[Edited on 29.8.13 by bfesser]

sargent1015 - 27-8-2013 at 04:54

Please post the actual article or a link to the article. You cannot make claims without backing it up with solid fact.

chemaddict - 28-8-2013 at 00:33

This is the refs that i should have posted first,sorry for that


thanks chemaddict




Attachment: Zinc_Ammonium Formate_ Rapid and selective reduction of oximes to amines - [www.rhodium.ws].html (19kB)
This file has been downloaded 1304 times

chemaddict - 28-8-2013 at 02:32

Well when the post got rendered as rubbish, i suppose i would not get a response then.
I don't no how many new members would just walk away from the site with that sort of welcoming, ! i mean to say i just asked a question.i thought this site was about helping people with an interest in chemistry to understand it.

but i guess i was wrong hey

thanks for the response



bfesser - 28-8-2013 at 06:48

A move to Beginnings does not mean that the post has been judged as "rubbish." Just settle down, and welcome to Science Madness!

chemaddict - 28-8-2013 at 16:25

the amount of replies will tell all

very disappointed

Ozone - 28-8-2013 at 17:44

Rubbish=Detritus.

Oximes are not nitro groups. The title probably threw a few people, including me.

I could have just as easily given you this:

http://books.google.com/books?id=XKP-mFbCs_0C&pg=PA133&a...

O3

[Edited on 29-8-2013 by Ozone]

chemaddict - 28-8-2013 at 18:42

I thank you very much ozone

the refs you provided cleared a lot of things up, but i have a couple of question to ask but i will wait until i have a in depth read of those papers.

i am a long time member of the forum but lost my user and password and had to register again,hence i don't no everything but i am not starting from scratch

regards chemaddict:o

bfesser - 28-8-2013 at 18:49

You don't remember your previous username? That shouldn't be too difficult to sort out. Also, I'm going to remove the capitalization from the subject of this topic&mdash;it's giving me a headache every time I check <img src="./images/xpblue/top_todaysposts.gif" /> <a href="today.php">Today's Posts</a>.

chemaddict - 28-8-2013 at 21:05

I no my user name but not my password



thanks ozone

chemaddict - 29-8-2013 at 03:08

getting back to chemistry

It is clear buy the information you provided ozone that hydroxyl amines can be reduced to amines with zinc and hydrochloric acid. But i have found no information that supports that zinc or other metals and hydrochloric acid will reduce oximes to amines without stopping at the hydroxyl amine, i suspect that the oxime is looking for more than one electron that zinc can provide,is this correct or can metal and acid be used for this also.

thanks ozone

Nicodem - 29-8-2013 at 10:00

Please UTFSE before opening topics that were already discussed and clarified, like this issue about the Abiraj and Gowda articles:
Reduction of oximes to corresponding amines
Mg/HCOONH4 oxime reduction...
oxime reductions
Reductions of Nitro groups with Zn and acid
Quote: Originally posted by chemaddict  
Well when the post got rendered as rubbish, i suppose i would not get a response then.
I don't no how many new members would just walk away from the site with that sort of welcoming, !

I really don't know why you had the need to render your post as rubbish. It really does not take much effort to write a post properly. If you need help for writing posts properly, you can always read the forum guidelines. However, I do agree with you. Posts like yours can cause new members to just walk away from the site. I certainly would not join this forum today, if the first few threads I read would have been like this one. Luckily, at the time I joined, I did so for other reasons, like locating some old friends, and only learned to love the forum later.

chemaddict - 29-8-2013 at 16:44

Hi Nicodem

Thanks heaps for the reply and the references you provided links to.
As for the references it is clear that the reductions of oximes with metal and formates is well known ,but in the information you provided there was members who have tried the zinc and acid reduction of oximes to amine but i am unable to find and solid proof or any mechanism to back it up .
My thoughts are that if zinc and acid can reduce hydroxylamines which is much more stable it can also reduce oximes, ! but maybe i am wrong.
Can someone provide any mechanism for this or can you verify that zinc and acid reduces oximes to amines



thanks chemaddict

chemaddict - 30-8-2013 at 00:39

As i thought this is as far as this post will go.

when the hard questions are asked,i suppose the answer to my question is no

thanks chemaddict

chemaddict - 30-8-2013 at 23:41

I suppose it might of well went to detritus , with no one willing to help . ! i thought that was the whole purpose of the forum
was to help people learn.
Well if this is as much interest members show to posts that people go to the time doing ,it makes me wonder why after 5 years why i bothered even returning.
At least with the 500 posts or so i have posted before i tried to help everyone as much as i could with my limited knowledge .

Buy the way Nicodem the zinc and acid reduction of oximes to amines was not clarified in earlier threads ,there is no references or mechanism to back it up , and i have utfse plenty of times most probably to help other people.

chemaddict

Nicodem - 31-8-2013 at 00:20

Quote: Originally posted by chemaddict  
As for the references it is clear that the reductions of oximes with metal and formates is well known

Known in what sense?
What is known up to now, is that the Indian article you cited is most likely the usual fictional work and most certainly contains non-scientific claims.
Quote:
but in the information you provided there was members who have tried the zinc and acid reduction of oximes to amine but i am unable to find and solid proof or any mechanism to back it up .

Why being so lazy? What sense does it make to ask others to do the literature work for you before you show any effort from your side? You could have easily found the references, if you would have read the literature searching instructions in the forum guidelines rather that wasting time with pathetic triple-posting of self-humiliating replies. Besides, a similar topic was already discussed in regard to aromatic nitro group reduction with metal dissolving reactions - for beginning, you might have followed those references:
Quote: Originally posted by Nicodem  
What is wrong with the general metal dissolving reaction mechanism for nitrobenzene to aniline reduction as presented in March's (chapter 19-45 Reduction of Nitro Compounds to Amines)? At least it involves no hydrogen abstraction, only simple electron and proton transfers, just as one would intuitively expect. The 6th edition has a nice scheme (page 1818) for the proposed mechanism and gives this reference: H.O. House, Modern Synthetic Reactions, 2nd ed., W.A. Benjamin, NY, 1972, p. 211. I suppose that is not the original reference, so those interested will have to hunt down the reference to the primary literature to get an answer.

Quote:
when the hard questions are asked,i suppose the answer to my question is no

You got it all wrong. On this forum, when simple questions are asked in a lazy and incomprehensible way, the answer is either silence or "go look it up yourself".
First rule of every human interaction: You get as much as you give.
Quote:
Buy the way Nicodem the zinc and acid reduction of oximes to amines was not clarified in earlier threads ,there is no references or mechanism to back it up , and i have utfse plenty of times most probably to help other people.

I'm pretty sure you did not read the threads I pointed you to. Either that or you did not understand the discussions.

chemaddict - 1-9-2013 at 14:03

Well i won't be coming back to this forum it is full of control freaks ,and ignorant an rude people.
The response i got to ask a simple question is a joke, when all that what needed was a yes or no .
all that everyone on this site wants to do is argue with each other and fuck people around.
This is not a happy place and not for me

nicodem
I'm pretty sure you did not read the threads I pointed you to. Either that or you did not understand the discussions.

i read them before i asked the question and i do understand, if you spent as much time giving people some answers as you did writing the reply it properly would save you a lot of time and help some people ,but the moderators i think are on some power freak medication .it is totally fucked .
things have not change here after 5 years