Zur 1.3-dipolaren cycloaddition aromatischer nitriloxide an azodicarbonsäureester
References (1)
Tetrahedron Letters
(1964)
Cited by (39)
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2011, TetrahedronCitation Excerpt :The following mechanistic postulate may be invoked to rationalise formation of the iminiphosphoranes. Initially zwitterion 51−3,24–27 generated from nucleophilic attack of triphenylphosphine upon diethyl azodicarboxylate 2 is protonated by the amine 1. Next, nucleophilic addition of the conjugate base of the NH-acid 7 on the phosphonium ion 6 give the adduct intermediate 8, which will be readily fragmentated under the reaction conditions to afford the isolated iminiphosphorane 3 by removal of diethyl 1,2-hydrazindicarboxylate 4 (Scheme 2).
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