Related Experiment Video
Updated: Aug 21, 2026

Versatile CO2 Transformations into Complex Products: A One-pot Two-step Strategy
Published on: November 9, 2019
C6H4 valence bond isomers: a reactive bicyclopropenylidene
Brian Halton1, Mark J Cooney, Carissa S Jones
1School of Chemical & Physical Sciences, Victoria University of Wellington, P.O. Box 600, Wellington, New Zealand. brian.halton@vuw.ac.nz
Abstract:
[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.
Related Concept Videos
Diels–Alder Reaction Forming Bridged Bicyclic Products: Stereochemistry
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group with both...
Aromatic Hydrocarbon Anions: Structural Overview
Due to the absence of continuous overlap of p...
Stability of Substituted Cyclohexanes
The two chair conformations of cyclohexanes undergo rapid interconversion at room temperature. Both forms have identical energies and stabilities, each comprising equal amounts of the equilibrium mixture. Replacing a hydrogen atom with a functional group makes the two conformations energetically non-equivalent.
For example, in...
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction
π Molecular Orbitals of 1,3-Butadiene
The simplest conjugated diene is 1,3-butadiene: a four-carbon system where each carbon is sp2-hybridized and has an unhybridized p orbital that contains an unpaired electron. According to molecular orbital theory, atomic orbitals combine to form molecular orbitals such that the number...

