A cyclopropabenzenylidenethenone (Propadienone) via a new route to alkylidenecycloproparenes

Halton, B., Dixon, G., Jones, C. M., Parkin, C. T., Naduvile Veedu, R., Bornemann, H. and Wentrup, C. (2005) A cyclopropabenzenylidenethenone (Propadienone) via a new route to alkylidenecycloproparenes. Organic Letters, 7 5: 949-952. doi:10.1021/ol050095f

Author Halton, B.
Dixon, G.
Jones, C. M.
Parkin, C. T.
Naduvile Veedu, R.
Bornemann, H.
Wentrup, C.
Title A cyclopropabenzenylidenethenone (Propadienone) via a new route to alkylidenecycloproparenes
Journal name Organic Letters   Check publisher's open access policy
ISSN 1523-7060
Publication date 2005-01-01
Sub-type Article (original research)
DOI 10.1021/ol050095f
Open Access Status Not Open Access
Volume 7
Issue 5
Start page 949
End page 952
Total pages 4
Place of publication Washington
Publisher Amer Chemical Soc
Language eng
Subject C1
250303 Physical Organic Chemistry
780103 Chemical sciences
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 degreesC ejects acetone and carbon dioxide, giving cyclopropabenzenylldenethenone 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.
Keyword Chemistry, Organic
Magnetic-resonance Spectra
Low-temperature Matrices
Cycloproparene Series
Meldrums Acid
Q-Index Code C1

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Created: Wed, 15 Aug 2007, 16:21:42 EST