Per the mechanism described here the reaction does not involve nitrene as an intermediate.(EDIT-1---I initially thought the written mechanism described so, but as Zhe points out,I was wrong in my observation.)

But, can anybody shed some light on why the reaction does not involve nitrene; though it possibly can?

  • 1
    $\begingroup$ The mechanism is similar to that of a Curtius, for which there have been a lot more mechanistic studies. The reaction is thought to be more concerted, avoiding the intermediate nitrene (which although proposed, has never been observed). $\endgroup$
    – NotEvans.
    Jun 23, 2017 at 17:21
  • $\begingroup$ I don't think the linked mechanism is quite correct $\endgroup$
    – Beerhunter
    Jun 23, 2017 at 18:49
  • $\begingroup$ Nitrenes are higher energy species; why make one when you can have a concerted migration that presumably proceeds via a lower energy pathway? $\endgroup$
    – Zhe
    Jun 26, 2017 at 14:44

1 Answer 1


Nowhere in that link is there a nitrene formed. All steps are concerted, that is, you see that alkyl shift happens at the same time as dinitrogen fragmentation.

So indeed, nitrenes are not intermediates. I suspect that mechanistic studies have been done. You might consider looking at this paper.


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