Cyclohexenol annulation via the alkoxy-accelerated rearrangement of vinylcyclobutanes

Regioselective SN2 Opening of Vinylic Epoxides with Trialkylzincates and Trialkylaluminates

“…The NMR spectra of 2b are identical to those reported previously. [36] trans-2-Butyl-3-cyclopenten-1-ol (6a): The product was isolated by FC (cyclohexane/EtOAc, 9:1) as a pale yellow oil. The NMR spectra of 6a are identical to those reported previously.…”

Cycloaddition and Electrocyclic Reactions of Vinylketenes, Allenylketenes, and Alkynylketenes

“…96,97 The reaction of methyl(vinyl)ketene with the electron-rich ethyl vinyl ether is more facile and also generates a mixture of stereoisomers (Scheme 61 The preference for formation of the more crowded products is also seen in reactions of 2-substituted vinylketenes with 1,3-cyclopentadiene and 1,3-cyclohexadiene, as exemplified by the ratio of products 44 and 45 in Scheme 62. 95 processes, as well as other reactions that compete with these cyclizations, and further transformations of initial products under the reaction conditions. The equilibrium between a vinylketene and the corresponding cyclobutenone involves one of the simplest of these processes.…”

Tricarbonyl(3-methoxybenzocyclobutenedione)chromium: Regioselective Nucleophilic Addition Reactions, Dianionic Oxy-Cope Rearrangements, Regioselective Intramolecular Aldol Additions, and a Rare Case of an Anionic 1-Vinylcyclobutenol−Cyclohexadienol Rearrangement

“…In this context, oxy anion driven ring-expansions of vinylcyclobutanols to cyclohexenols and subsequently to cyclohexanones Ϫ so-called vinylcyclobutane rearrangements Ϫ have been the subject of some investigations. Danheiser reviewed the matter in 1991, [28] showing that rearrangements of oxy anion driven 1-vinylcyclobutoxides are much rarer than those of 2-vinylcyclobutoxides. In addition, it is known that both uncoordinated and coordinated 1-hydroxybenzocyclobutenes undergo an oxy anion driven ring-opening to an oxy anion substituted ortho-quinodimethane at low temperature.…”