A Cyclopropabenzenylidenethenone (propadienone) via a new route to alkylidenecycloproparenes.
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]
Halton
Brian
B
School of Chemical & Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington, New Zealand. brian.halton@vuw.ac.nz
Dixon
Gareth M
GM
Jones
Carissa S
CS
Parkin
Christopher T
CT
Veedu
Rakesh N
RN
Bornemann
Holger
H
Wentrup
Curt
C