135441-19-9Relevant academic research and scientific papers
Nucleophilic additions to tricyclodecadienone epoxides. The Payne rearrangement of α,β-epoxycyclopentanols contained in a rigid tricyclic system
Dols, Paul P. M. A.,Arnouts, Esther G.,Rohaan, Johannes,Klunder, Antonius J. H.,Zwanenburg, Binne
, p. 3473 - 3490 (1994)
Organometallic reagents add regio- and stereoselectively from the convex exo-face to the carbonyl function of exo-4,5-epoxytricyclodecenones 5 and 8 to give tricyclic exo-epoxy-endo-alcohols 6 and 9, respectively. These initial adducts can undergo a Payne
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 (2007/10/02)
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.
