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Microwave-promoted synthesis of bicyclic azocine-β-lactams from Bis(allenes)

AuthorsAlcaide, Benito ; Almendros, Pedro ; Aragoncillo, Cristina; Fernández, Israel; Gómez-Campillos, Gonzalo
Issue Date2014
PublisherAmerican Chemical Society
CitationJournal of Organic Chemistry 79: 7075- 7083 (2014)
AbstractA 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.
Identifiersdoi: 10.1021/jo501231q
issn: 0022-3263
e-issn: 1520-6904
Appears in Collections:(IQOG) Artículos
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