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Synlett 1993; 1993(1): 9-19
DOI: 10.1055/s-1993-22330
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Gas Phase Chemistry of Ketenes, Carbenes, Acetylenes and Arynes: Synthetic Consequences

Roger F. C. Brown* , Frank W. Eastwood
  • *Department of Chemistry, Monash University, Clayton, Victoria 3168, Australia
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Publication Date:
19 March 2002 (online)

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The development of methyleneketene and methylenecarbene chemistry is outlined, and its relationship to recent gas phase synthetic reactions involving acetylene - methylenecarbene and aryne - exocyclic carbene rearrangements is described. Such synthetic reactions offer new approaches to polycyclic aromatic compounds, particularly those containing five-membered rings. 1. Introduction 2. Generation of Ketenes by FVP 3. Syntheses Based on Intramolecular Reactions of Substituted Methyleneketenes 4. Generation and Rearrangement of Acyloxycarbenes 5. Syntheses Based on the Acetylene to Methylenecarbene Rearrangement 6. Generation of Benzyne by FVP and the Benzyne to Cyclopentadienylidenecarbene Rearrangement 7. Syntheses Based on Intramolecular Trapping of Cyclopentadienylidenecarbenes 8. Conclusion