Bullvalene

Bullvalene is a hydrocarbon with the chemical formula C₁₀H₁₀ with the unusual property that the chemical bonds making up the molecule are constantly rearranging as in fluxional molecules. For this reason bullvalene is extensively studied in organic chemistry.

Origin of the name

The name bullvalene is derived from the nickname of one the scientists who predicted its properties in 1963 and the underlying concept of valence tautomerism,William "Bull" Doering. According to Klärner in 2011, the weekly seminars organised by Doering were secretly called "Bull sessions" by PhD students and postdocs and "were feared by those who were poorly prepared". The name was bestowed on the molecule, in 1961, by two of Doering's Yale graduate students: Maitland Jones (now at NYU) and Ron Magid (retired from University of Tennessee). The name celebrates Bill Doering's well-known nickname and was chosen to rhyme with fulvalene, a molecule of great interest to the research group.

Stereodynamics

The bullvalene molecule is a cyclopropane platform with three vinyl arms conjoined at a methine group. As a fluxional molecule, bullvalene is subject to degenerate Cope rearrangements, with the result that all carbon atoms and hydrogen atoms appear equivalent on the NMR timescale. The number of possible valence tautomers is 10, since any of the 10 carbon atoms may be at the "apex".