[wisconsinium]

I want to deprotonate a dithiane compound which also has a nitro group. Is the nitro group compatible with BuLi? I don't see what could be wrong, but it just seems weird... thoughts?
Thanks

[willug]

Do you have any protons α to the nitro group? They would be activated, and that might cause you some problems...

[AlphaScent]

It should not.  The nitro group is electron withdrawing and would add to acidity of the protons on the six-membered ring.  Protons alpha to the nitro group will become activated and will be removed by butyllithium.

could you give a structure?

[willug]

What I mean is if you are planning on deprotonating your dithiane and quencing it with an electrophile, then that same mode of reactivity might also occur alpha to a nitro group somewhere else in the molecule. Which could be a problem if that wasn't desired.

[wisconsinium]

the compound is 2-nitrophenyl-1,3-dithiane. so no alpha protons. thanks

[g-bones]

I don't think it will be an issue, but be aware of nucleophilic attack on oxygen of the nitro.  Similar to Bartoli indole synthesis. 

[AlphaScent]

If you are talking about a 1,3-thiane where there is a sulfur atom at the one and three position, with two total cyclic rings; then there would be alpha hydrogens.

example: http://www.molport.com/buy-chemicals/moleculelink/2-2-nitrophenyl-1-3-dithiane/3908170

I do understand that its not the same, but are saying there is a thiane ring on either side of the nitrogroup?
 

[Doc Oc]

This is an umpolung reaction.  The dithiane is a masked carbonyl which can be used as a nucleophile with a strong enough base.

The nitro group on the aromatic ring shouldn't interfere, but it all depends on what you're trying to do and the reaction conditions.

[orgopete]

2-nitrotoluene is reasonably easily deprotonated. I don't think you need to use butyllithium.

[discodermolide]

If you are talking about a 1,3-thiane where there is a sulfur atom at the one and three position, with two total cyclic rings; then there would be alpha hydrogens.

example: http://www.molport.com/buy-chemicals/moleculelink/2-2-nitrophenyl-1-3-dithiane/3908170

I do understand that its not the same, but are saying there is a thiane ring on either side of the nitrogroup?
 

Think of the work by Sniekus on ortho metalation.
have a look here:
http://www.chem.queensu.ca/people/faculty/Snieckus/publications.html

[AlphaScent]

If you are talking about a 1,3-thiane where there is a sulfur atom at the one and three position, with two total cyclic rings; then there would be alpha hydrogens.

example: http://www.molport.com/buy-chemicals/moleculelink/2-2-nitrophenyl-1-3-dithiane/3908170

I do understand that its not the same, but are saying there is a thiane ring on either side of the nitrogroup?
 

I feel silly, but I am not making the connection with this work.  I did not see any thiane, nor dithianes.

Think of the work by Sniekus on ortho metalation.
have a look here:
http://www.chem.queensu.ca/people/faculty/Snieckus/publications.html

[discodermolide]

If you are talking about a 1,3-thiane where there is a sulfur atom at the one and three position, with two total cyclic rings; then there would be alpha hydrogens.

example: http://www.molport.com/buy-chemicals/moleculelink/2-2-nitrophenyl-1-3-dithiane/3908170

I do understand that its not the same, but are saying there is a thiane ring on either side of the nitrogroup?
 

I feel silly, but I am not making the connection with this work.  I did not see any thiane, nor dithianes.

Think of the work by Sniekus on ortho metalation.
have a look here:
http://www.chem.queensu.ca/people/faculty/Snieckus/publications.html

The fact is that aromatic rings with a certain substation pattern can undergo metalisation and consequently be alkylated at the position ortho to the substituent.
Now if you have an aromatic ring with a nitro group, as we have in this case, it could, with butyl lithium or similar base undergo ortho metalisation and be alkylated with an electrophile. So we could very well get interference from the aromatic nitro group in this example from the OP. Quote "the compound is 2-nitrophenyl-1,3-dithiane"
 

[orgopete]

The protons of a nitrotoluene are relatively acidic and the ortho metalation described by Snieckus may not be necessary. For example, o-nitrotoluene will react with DMF dimethylacetal to produce a nitrostyrene directly, see http://www.orgsyn.org/orgsyn/prep.asp?prep=cv7p0034.

This is a half-a-loaf type of question. We really don't know what is being done, so it is difficult to suggest what might happen. None the less, if an anion is prepared in which an acinitro form participates in its stability, I would also caution about the possibility of the acinitro-anion participating in the next step. Certainly this is a problem for anions of nitroalkanes. I don't know if it might also be a problem for an aromatic nitro group.

[opsomath]

nBuLi will directly reduce a nitro group, probably by O-centered nucleophilic attack like another poster said, unless there is a more reactive group such as an acidic proton - even then, careful choice of conditions is needed.

[discodermolide]

nBuLi will directly reduce a nitro group, probably by O-centered nucleophilic attack like another poster said, unless there is a more reactive group such as an acidic proton - even then, careful choice of conditions is needed.

Do you have a reference for this reduction?
BuLi is not normally considered a reducing agent.