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Updated: Jul 26, 2025

Preparation of Contiguous Bisaziridines for Regioselective Ring-Opening Reactions
Published on: July 28, 2022
Cyaphide-Azide 1,3-Dipolar Cycloaddition Reactions: Scope and Applicability
Eric S Yang1, Alex Mapp1, Andrew Taylor1
1Department of Chemistry, University of Oxford, Chemistry Research Laboratory, 12 Mansfield Rd., Oxford, OX1 3TA, U.K.
Abstract:
Several examples of the cyaphide-azide 1,3-dipolar cycloaddition reaction to afford metallo-triazaphospholes are reported. The gold(I) triazaphospholes Au(IDipp)(CPN3 R) (IDipp=1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene; R=t Bu, Ad, Dipp), magnesium(II) triazaphospholes, {Mg(Dipp NacNac)(CPN3 R)}2 (Dipp NacNac=CH{C(CH3 )N(Dipp)}2 , Dipp=2,6-diisopropylphenyl; R=t Bu, Bn), and germanium(II) triazaphosphole Ge(Dipp NacNac)-(CPN3 t Bu) can be prepared straightforwardly, under mild conditions and in good yields, in a manner reminiscent of the classic alkyne-azide click reaction (albeit without a catalyst). This reactivity can be extended to compounds with two azide functional groups such as 1,3-diazidobenzene. It is shown that the resulting metallo-triazaphospholes can be used as precursors to carbon-functionalized species, including protio- and iodo-triazaphospholes.
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