Ozonolysis of nitronate

What is the mechanism for the ozonolysis of a nitronate anion? What gas is produced in this reaction? Is there any chemoselectivity in the presence of a double C=C bond in the molecule?





> 
> What is the mechanism for the ozonolysis of a nitronate anion? 
> 
> 
> 


Probably very analogous to ozonolysis of a double bond.


![enter image description here](https://i.stack.imgur.com/Rh5FF.jpg)


A typical synthetic procedure is detailed in [OrgSyn](http://www.orgsyn.org/demo.aspx?prep=cv6p0648). Note the addition of dimethylsulfide during work-up; this is common in ozonolysis reactions as it helps reduce the ozonide and also reduces any other dangerous, highly oxidized by-products. The discussion section of the OrgSyn article says,



> 
> "There are various methods available for transforming a nitro group
>  into a carbonyl group, including the Nef reaction (strongly acidic),²
>  permanganate oxidation of nitronate anions (basic, oxidative),³
>  persulfate oxidation of nitronates (basic, oxidative),⁴ treatment with
>  a mixture of organic and inorganic nitrite (neutral, oxidative),⁵ and
>  treatment of either a free nitro compound or a nitronate anion with
>  aqueous titanium(III) (neutral, reductive).⁶ Each method is limited,
>  however, by poor yield, inconvenience, or lack of generality.
> 
> 
> With the proviso that the substrate not contain a reactive
>  carbon-carbon double bond, the present ozonolysis procedure⁷ appears
>  to provide a convenient and efficient method for carrying out the
>  desired "
> 
> 
> 


The [Nef Reaction](http://en.wikipedia.org/wiki/Nef_reaction) is mentioned above, it is worth taking a look at the linked article since the Nef reaction is complementary to the ozonolysis reaction of nitronates. You may also find the "Reaction mechanism" section interesting.



> 
> What gas is produced in this reaction? 
> 
> 
> 


According to the above mechanism, no gas would be generated, rather $\ce{NO3^{-}}$ is produced



> 
> Is there any chemoselectivity in the presence of a double C=C bond in the molecule?
> 
> 
> 


No, as mentioned in the OrgSyn reference, this approach can't be used when other double bonds are present.


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