72173-01-4Relevant academic research and scientific papers
Electrophilic Opening of Photochemically Generated Bicyclopentane Derivatives - A Two-Step 3,3-Dimethylcyclopentane Anellation
Misslitz, Ulf,Primke, Hartmut,Meijere, Armin de
, p. 537 - 544 (2007/10/02)
Tricyclic compounds 7a-e with 5,5-dimethylbicyclopentane subunits were obtained - although in poor yields - by photochemically initiated cycloaddition of 3,3-dimethylcyclopropene to 2-cycloalken-1-ones 4a-e.Catalytic hydrogenation of bicyclopentanes 7a/7c proceeded regioselectively to give bicyclic compounds 17a/17c with gem-dimethyl-substituted cyclopentane units.Treatment of carbonyl-protected bicyclopentanes 16a/16c with mercury(II) acetate in THF/water or THF/methanol followed by reductive demercuration afforded - with practically quantitative diastereo-, but no recognizable regioselectivity - gem-dimethyl-substituted hydroxy- or methoxycyclopentanes 18-21, respectively.Upon warming under reflux the hydroxymercurated ketone 7c gave the regioselectively formed β-elimination product endo-7-hydroxy-8,8-dimethylbicyclonon-1(9)-en-2-one (23).Upon analogous treatment, however, hydroxymercurated 7a was recovered unchanged. - Keywords: Cycloaddition of 3,3-dimethylcyclopropene/ Ring-anellated bicyclopentanes/ Hydroxymercuration of bicyclopentanes/ 3,3-Dimethylcyclopentane anellation
