Halodecarboxylation Reaction of 4‐Alkylidene‐β‐lactams | Zendy

Galletti Paola | Zendy; Quintavalla Arianna | Zendy; Ventrici Caterina | Zendy; Giacomini Daria | Zendy

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Halodecarboxylation Reaction of 4‐Alkylidene‐β‐lactams

Author(s) -

Galletti Paola,

Quintavalla Arianna,

Ventrici Caterina,

Giacomini Daria

Publication year - 2009

Publication title -

european journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.825

H-Index - 155

eISSN - 1099-0690

pISSN - 1434-193X

DOI - 10.1002/ejoc.200900558

Subject(s) - chemistry , triethylamine , reaction conditions , coupling reaction , reaction mechanism , dimethylzinc , combinatorial chemistry , organic chemistry , stereochemistry , medicinal chemistry , catalysis

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)

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