135441-24-6Relevant academic research and scientific papers
TRICYCLO2,6>DECADIENONE EPOXIDES: RIGID, HIGHLY CONGESTED α,β-EPOXYCYCLOPENTANONES WITH DISTINCTIVE CHEMICAL BEHAVIOR.
Lange, J. H. M.,Sommerdijk, N. A. J. M.,Dols, P. P. M. A.,Arnouts, E. G.,Klunder, A. J. H.,Zwanenburg, B.
, p. 3127 - 3130 (1991)
Tricyclodecadienone epoxides 5 do not form an enolate on treatment with lithium diisopropyl amide, but instead undergo an unusual stereoselective β-hydride transfer leading to alcohols 6.The same type of epoxy endo-alcohol was obtained from parent epoxy ketone 5 on reaction with metal hydrides and organolithium reagents.These alcohols readily undergo an intramolecular epoxide migration by a Payne-type rearrangement, to give endo-epoxides 9.
