Why are trifluoromethyl diazirines so stable? Trifluoromethyl diazirines stability is well documented, however I am yet to find an explanation of why... Can it be homoaromatic or even aromatic? 2 pie e-, in a planar system? Even with the sp3 carbon, couldn't that make it homoaromatic?

Or is it just aided by the trifluoromethyl group withdrawing electrons from the strained ring?

Bonus points of you know the mechanism of Schmitz Diaziridine/diazirine synthesis.

Any resources or insight is greatly appreciated.

Thanks, James

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    $\begingroup$ related jbc.org/content/255/8/3313.full.pdf $\endgroup$ – Mithoron Oct 10 '15 at 13:52
  • $\begingroup$ Thanks, yeah I've seen that. Seems to show the conditions it can survive, but not explanation of why or mechs (unless I missed it). $\endgroup$ – James Oct 11 '15 at 12:04

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