A compound to which the reaction rule is not applicable.

Hi.

I am facing a problem. I have one compound to which reaction rule is not applicable.

The reaction is called Criegee reaction which is the reaction of ozone with olefinic group to form ozonide.

Here I attached the file showing reactions. I tested 4 similar compounds.

You can see that only one compound, No. 1(Pyrimidine), is not reacting with ozone so the reactor only showed 3 results out of 4 reactants. 

I can't figure out why this reaction doesn't take place.

Please let me know.. what is the problem..

 

Hi,

The uracil derivative in your first example comes up as an aromatic ring due to Reactors' aromatization system, thus the scheme and the first example do not match anymore. 

I would recommend you modify the scheme, please find my suggestion below (ozonide-revised.jpg).  I changed the 'double bond' to a 'double-or-aromatic bond', I removed the R groups (they do not describe any special atoms or groups) and I also mapped all of the oxygens. 

I also would add the following reactivity rules to your reaction:

(match(ratom(1), "[C:1]=[C:2]", 1) 


and match(ratom(2), "[C:1]=[C:2]", 2))


or (match(ratom(1), "O=c1[c:1]([C,H])[c:2]([C,H])nc(=O)n1", 1)


and match(ratom(2), "O=c1[c:1]([C,H])[c:2]([C,H])nc(=O)n1", 2))

Nevertheless, you can remove O₃ as a reactant from the scheme thus you do not need to add it as a reagent to each example, respectively. Your reaction will work properly. (ozonide-revision-2.jpg)

 

I hope the answers solve your problem!

Hi.

Thank you for your answer and suggestion.

I made a mistake.. when I checked the original reference yesterday I found that there is another reaction before forming ozonide which is the formation of O3 adduct at C5. So I don't need to include aromatic bond in my reaction.

I kept making mistakes.:) It's obvious that the carbon with hydroxyl group for the other 3 compounds above has sp3 hydridization so conjugation system over the ring cannot be formed.

I should have been careful before I asked you. I am very sorry to bother you too much.

Once again thank you very much.