Efficient two-step synthesis of 3-halo-3-enals or 2-halo-2-alkenyl ketones from propargylic bromides via a unique cationic 1,2-aryl or proton shift in electrophilic addition reaction of 2,3-allenols with X+
Literature Information
Chunling Fu, Jing Li
The reaction of readily available 1-substituted 2,3-allenols with Br2, NBS, or I2 afforded the not-easily-available but synthetically useful 3-halo-3-alkenals or 2-halo-2-alkenyl ketones in good yields via a sequential electrophilic interaction of X+ with the allene moiety , a 1,2-aryl or proton shift, and a H+-elimination process; the structures of the products were established by X-ray diffraction study.
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![4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione structure 4-[(2-{2-[2-(2-Aminoethoxy)ethoxy]ethoxy}ethyl)amino]-2-(2,6-dioxo-3-piperidinyl)-1H-isoindole-1,3(2H)-dione structure](https://static.chemtradehub.com/structs/209/2093416-31-8-3162.webp)



