The Nitrile Imine 1,3-Dipole by Craig Jamieson & Keith Livingstone

Author:Craig Jamieson & Keith Livingstone
Language: eng
Format: epub
ISBN: 9783030434816
Publisher: Springer International Publishing

Alternatively, the inclusion of an ortho-nitro aryl group on the N-terminus of the NI can lead to a 1,7-type rearrangement, generating the seven membered-ring shown as the primary product (Scheme 3.72) [222–224]. An extensive rearrangement process sees the eventual isolation of a hydroxy triazole derivate from the reaction mixture [225].

Scheme 3.72The rearrangement of NIs containing an o-NO2 group within the N-Ar ring

With multiple forms of rearrangement possible, from both the C and N termini of the NI, it should be noted that competition experiments between the different processes discussed herein have shown that 1,5-rearrangements of the N-terminus are favoured over any such reaction at the C-terminus [226].

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