Journal article
A Cyclopropabenzenylidenethenone (Propadienone) via a New Route to Alkylidenecycloproparenes
Organic Letters, Vol.7(5), pp.949-952
2005
Abstract
Reaction of 1,1-dichloro-2,5-diphenylcyclopropabenzene 6 with Meldrum's acid 8 in the presence of pyridine leads to coupling of the cycloproparenyl cation 7 with the stabilized diketo anion 9. Subsequent, spontaneous, base-induced dehydrochlorination gives the alkylidenecyclopropabenzene 11 in a one-pot reaction. Flash vacuum thermolysis of 11 at 650 °C ejects acetone and carbon dioxide, giving cyclopropabenzenylidenethenone 12 that is isolated in an Ar matrix at 20 K and characterized by a strong ketene band at 2107 cm-1 in the IR spectrum.
Details
- Title
- A Cyclopropabenzenylidenethenone (Propadienone) via a New Route to Alkylidenecycloproparenes
- Authors/Creators
- B. Halton (Author/Creator)G.M. Dixon (Author/Creator)C.S. Jones (Author/Creator)C.T. Parkin (Author/Creator)R.N. Veedu (Author/Creator)H. Bornemann (Author/Creator)C. Wentrup (Author/Creator)
- Publication Details
- Organic Letters, Vol.7(5), pp.949-952
- Publisher
- ACS Publications
- Identifiers
- 991005541541507891
- Copyright
- © 2005 American Chemical Society
- Murdoch Affiliation
- Murdoch University
- Language
- English
- Resource Type
- Journal article
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- Collaboration types
- Domestic collaboration
- International collaboration
- Citation topics
- 2 Chemistry
- 2.1 Synthesis
- 2.1.1085 Aromaticity
- Web Of Science research areas
- Chemistry, Organic
- ESI research areas
- Chemistry