118465-27-3Relevant academic research and scientific papers
Some novel electron transfer mediated cascade ring-opening reactions of bicyclo[4.1.0]ketones
Batey, Robert A.,Harling, John D.,Motherwell, William B.
, p. 11421 - 11444 (2007/10/03)
The radical ring-opening reactions of cyclopropyl ketones, mediated by samarium (II) iodide and other electron transfer agents are described. This strategy allows tandem rearrangement cyclisation reactions and the trapping of the resultant samarium (III) enolates by a variety of electrophiles, for the construction of complex bicyclic systems.
SOLVOLYSIS OF 3-ALKENYL-2-CYCLOHEXENYL ESTERS
Jursic, Branko,Ladika, Mladen,Bosner, Branka,Kobetic, Renata,Sunko, Dionis E.
, p. 2311 - 2318 (2007/10/02)
In an attempt to study possible ?-participation in allyl-dervatives, 3-alkenyl-5,5-dimethyl-2-cyclohexenyl p-nitrobenzoates 4 and 2-alkenyl-3-methyl-2-cyclohexenyl p-nitrobenzoates 5 were solvolyzed in 97 wt percent trifluoroethanol and 80 vol percent ethanol.Water soluble 1-methyl-3-(3-alkenyl-5,5-dimethyl-2-cyclohexenyl)pyridinium iodides 6 were solvolyzed in water and in aqueous solvents, as well as under micellar conditions.All esters show in each of the solvents normal values of secondary α-deuterium isotope effects (kH/kD = 1.17-1.23).Also in comparison to saturated analogues the investigated esters show a lower solvolytic reactivity.On the basis of these results it was concluded that the solvolysis proceeds via a stepwise mechanism involving a resonance-stabilized cyclohexenyl cation as the reaction intermediate.
