PhI(OAc)2‐Promoted 1, 2‐Diaza‐Cope Rearrangement of β, γ‐Unsaturated Hydrazones with Acetate/H2O: Access to Diacyl/Acyl N‐Allylhydrazines. Issue 33 (13th August 2020) - Fang, Zhuo‐Yue
Abstract : A novel metal‐free methodology for the synthesis of diacyl/acyl N ‐allylhydrazines based on PhI(OAc)2 ‐promoted 1, 2‐diaza‐Cope rearrangement reaction of β, γ‐unsaturated hydrazones with acetate/H2 O has been described. This cascade reaction works efficiently under mild conditions. A possible mechanism involving hydrazonyl radicals and N–I(III) intermediates of β, γ‐unsaturated hydrazones is proposed. Abstract : A novel metal‐free methodology for the synthesis of diacyl/acyl N ‐allylhydrazines based on PhI(OAc)2 ‐promoted 1, 2‐diaza‐Cope rearrangement reaction of β, γ‐unsaturated hydrazones with acetate/H2 O has been described. This cascade reaction works efficiently and features good substrate tolerance under mild conditions. A possible mechanism involving hydrazonyl radicals and N–I(III) intermediates of β, γ‐unsaturated hydrazones is proposed.