Unexpected C-C cleavage: 1,2,4-oxadiazol-5-one fm. amidoximes w/ penta-F-Ph \ 3-F-Me

[Nagelfar]

I found this late 2011 paper interesting. I was looking for information on tri-fluoro-methyls as leaving groups and found this:

 

[belligerent drunk]

Interesting article, but what's your point? Considering even chloroform's hydrogen is pretty acidic, I don't imagine trifluoromethyl group would be a terrible leaving group under proper conditions, especially because in this case its an intramolecular substitution (the C-C cleavage).

Synthesis discussion is generally unacceptable here.

 

[adder]

I don't think this is that unusual, under proper conditions (that is with a strong enough nucleophile) even phenyl group can be a leaving group, e.g. nucleophilic substitution in sulfoxides or phosphine oxides, although at the time of the discovery this may not have been so obvious and predicted to happen. I suppose your main interest in this is to quickly apply the resulting cyclic moiety to make a new phenyltropane, am I right?