1196989-62-4Relevant academic research and scientific papers
Divergent reactivity in tandem reduction - Michael ring closures of five- and six-membered cyclic enones
Bunce, Richard A.,Nammalwar, Baskar,Slaughter, LeGrande M.
experimental part, p. 854 - 860 (2009/12/24)
(Chemical Equation Presented) In this study, methyl (±)-1-(2- nitrobenzyl)-4-oxo-2-cyclohexene-1-carboxylate and methyl (±)-(2- nitrobenzyl)-4-oxo-2-cyclopentene-1-carboxylate were prepared and subjected to reductive cyclization under dissolving metal conditions. The two reactants showed divergent behavior with the six-ring substrate reacting at the ester carbonyl and the five-ring substrate closing on the enone double bond. The difference in reactivity is attributed to the conformational flexibility, relative reactivity, and steric environment of C4-substituted six- and five-membered cyclic enones.
