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)

• Record Type: Journal Article
• Authors: Fang, Zhuo‐Yue; Qi, Lin; Song, Jin‐Yan; Ren, Pei‐Xing; Hou, Cong‐Ying; Ji, Shi‐Chao; Wang, Li‐Jing; Li, Wei
• Is Part Of: European journal of organic chemistry. Issue 33(2020)
• Page Start: 5464
• Page End: 5468
• Publication Date: 2020-08-13
• Subjects: Cope rearrangement -- Hydrazones -- Pericyclic reactions -- Synthetic methods; Chemistry, Organic -- Periodicals; Organic compounds -- Synthesis -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1002/ejoc.202000875
• Languages: English
• ISSNs: 1434-193X

Abstract

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.