Halodecarboxylation Reaction of 4‐Alkylidene‐β‐lactams

Abstract

Abstract The synthesis of halo‐ and dihalovinyl‐β‐lactams by a halodecarboxylation reaction has been developed. Optimized procedures gave good yields of dibromo‐, iodo‐ and diiodovinyl derivatives. The unprecedented synthesis of dihalo compounds by a Hunsdieker reaction was investigated in detail by 1 H NMR analysis, which allowed the formulation of a reaction mechanism and revealed the role of triethylamine as a deiodinating agent. The dibromo‐ and diiodoalkylidene‐β‐lactams obtained were tested in a cross‐coupling reaction with dimethylzinc. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)