A Cyclopropabenzenylidenethenone (propadienone) via a new route to alkylidenecycloproparenes |
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| Authors: | Halton Brian Dixon Gareth M Jones Carissa S Parkin Christopher T Veedu Rakesh N Bornemann Holger Wentrup Curt |
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| Affiliation: | School of Chemical & Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington, New Zealand. brian.halton@vuw.ac.nz |
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| 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 degrees 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. [reaction: see text] |
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