title: Microwave-promoted synthesis of bicyclic azocine-β-lactams from bis(allenes).
abstract: A metal-free preparation of structurally novel bicyclic azocine-β-lactams has been developed. The first examples accounting for the preparation of eight-membered rings from bis(allenes) in the absence of metals have been achieved by the thermolysis of nonconjugated 2-azetidinone-tethered bis(allenes) on application of microwave irradiation. This selective carbocyclization reaction has been studied experimentally, and additionally, its mechanism has been investigated by a DFT study.
authors.affiliation: Grupo de Lactamas y Heterociclos Bioactivos, Departamento de Quı́mica Orgánica I, Unidad Asociada al CSIC, Facultad de Quı́mica, Universidad Complutense de Madrid , 28040 Madrid, Spain.
authors.forename: Benito
authors.initials: B
authors.lastname: Alcaide
authors.forename: Pedro
authors.initials: P
authors.lastname: Almendros
authors.forename: Cristina
authors.initials: C
authors.lastname: Aragoncillo
authors.forename: Israel
authors.initials: I
authors.lastname: Fernández
authors.forename: Gonzalo
authors.initials: G
authors.lastname: Gómez-Campillos
mesh_terms: D000466:Alkadienes / Q000737:chemistry*; D001392:Azocines / Q000138:chemical synthesis* / Q000737:chemistry; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D008872:Microwaves; D015394:Molecular Structure; D011789:Quantum Theory; D047090:beta-Lactams / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000466:Alkadienes; D001392:Azocines; D019086:Bridged Bicyclo Compounds, Heterocyclic; D047090:beta-Lactams; C025947:propadiene