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Author

CARTWRIGHT, HELENA, Andrews, Tina, Smith, Paula, Halton, B., and Taylor, Christine

Published
2020

8. A Cyclopropabenzenylidenethenone (Propadienone) via a New Route to Alkylidenecycloproparenes

Author

Halton, B., Dixon, G.M., Jones, C.S., Parkin, C.T., Veedu, R.N., Bornemann, H., Wentrup, C., Halton, B., Dixon, G.M., Jones, C.S., Parkin, C.T., Veedu, R.N., Bornemann, H., and Wentrup, C.

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.

Published
2005

48. C<INF>6</INF>H<INF>4</INF> Valence Bond Isomers:  A Reactive Bicyclopropenylidene

Author

Halton, B., Cooney, M. J., Jones, C. S., Boese, R., and Blaser, D.

Abstract

The simple bicyclopropenylidene derivative 21b, stabilized by fusion into naphthalene, results from reaction of dimesitylcyclopropenone 20b with the 1-trimethylsilyl-1H-cyclopropa[b]naphthalenyl anion. Although unstable in air, the molecule survives ambient conditions long enough for separation and mass spectral characterization. Aerial oxidation of 21b leads to 2,3-dimesitylanthracene-1,4-dione 22b whose X-ray crystal structure has been determined. While diphenylcyclopropenone 20a does not give identifiable products, the di-tert-butyl analogue 20c gives quinone 22c but in lower yield.

Published
2004

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