Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2011, Issue 2, Pages 364-370Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201001233
Keywords
Allenes; Alkynes; Cyclization; Lactams; Radicals; Small ring systems
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Funding
- Direccion General de Investigacion - Ministerio de Ciencia e Innovacion (DGI-MICINN) [CTQ2009-09318]
- Universidad Complutense-Banco Santander (UCM-BSCH) [GR58/08]
- Comunidad Autonoma de Madrid (CAM) [S2009/PPQ-1752]
- MICINN
- European Social Fund
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A thermal methodology for the expeditious preparation of structurally novel strained tricyclic beta-lactams containing a cyclobutene ring has been developed. Besides, the first examples accounting for the intramolecular double [2+2] cycloaddition of bis(allenyne)s have been achieved through thermolysis of C-2-symmetric or unsymmetric bis(beta-lactam-allenyne)s, which have been prepared by copper-promoted alkyne homo- or cross-coupling reactions. The bis(tricyclic) ring structures bearing a central seven-membered ring arise from the regioselective cyclization of the alkyne with the distal bond of the allene, most likely via a radical intermediate.
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