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A Cyclopropabenzenylidenethenone (Propadienone) via a New Route to Alkylidenecycloproparenes

Halton, B., Dixon, G.M., Jones, C.S., Parkin, C.T., Veedu, R.N., Bornemann, H. and Wentrup, C. (2005) A Cyclopropabenzenylidenethenone (Propadienone) via a New Route to Alkylidenecycloproparenes. Organic Letters, 7 (5). pp. 949-952.

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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.

Item Type: Journal Article
Publisher: ACS Publications
Copyright: © 2005 American Chemical Society
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