C6H4 valence bond isomers: a reactive bicyclopropenylidene.
[reaction: see text] 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.
Halton
Brian
B
School of Chemical & Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington, New Zealand. brian.halton@vuw.ac.nz
Cooney
Mark J
MJ
Jones
Carissa S
CS
Boese
Roland
R
Bläser
Dieter
D