That variation is used to synthesize gamma-epsilon unsaturated ketones via tautomerization, and is known as the oxy- type.
Gajewski defined the bond-making and bond-breaking secondary kinetic isotope effects to determine the mechanism of this reaction. Vogel and Wharton found that it can be accelerated by strain, and another study by Roth and Doering showed that its intermediate preferred the chair conformation over the boat one. The aza- variant can be combined with an intermolecular Mannich reaction to form pyrrolidines. This reaction leads to rapid fluxional interconversion of bullvalene, and one variation is accelerated by deprotonation of a hydroxyl substituent. That variation is used to synthesize gamma-epsilon unsaturated ketones via tautomerization, and is known as the oxy- type. Like Diels-Alder, there's confusion whether there's a diradical or concerted intermediate in this reaction, and it proceeds via the suprafacial route. Sharing its namesake with an elimination of amine oxide, for 10 points, name this sigmatropic rearrangement of 1,5-dienes, named for an American.
Gajewski defined the bond-making and bond-breaking secondary kinetic isotope effects to determine the mechanism of this reaction.
{Cope} rearrangement