Bullvalene

This pattern is consistent with an exchange process whose rate k is close to the frequency separation of the four contributing resonances.

[7] Semibullvalene exists only as two valence tautomers (2a and 2b in scheme 3) but in this molecule the Cope rearrangement takes place even at -110 °C, a temperature at which this type of reaction is ordinarily not possible.

Both are named after Barbara M. Ferrier,[10] (1932–2006) professor of the Department of Biochemistry and Biomedical Sciences at McMaster University.

[11] The name bullvalene is derived from the nickname of one of the scientists who predicted its properties in 1963 and the underlying concept of valence tautomerism,[12] William "Bull" Doering.

[13][14] 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".

[15] The name was bestowed on the molecule, in 1961, by two of Doering's Yale graduate students, Maitland Jones Jr and Ron Magid.

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.

Scheme 2. A bullvalone
Scheme 3. Semibullvalene synthesis
Scheme 4. Barrelene photolysis mechanism
Scheme 5. New semibullvalene synthesis