2565-93-7Relevant academic research and scientific papers
On the Stereochemistry of Grignard Addition to Bicyclononan-2-one. Preferential Axial Attack on a Cyclohexanone System by a Bulky Nucleophile
Guerriero, Antonio,Pietra, Francesco,Cavazza, Marino,Cima, Francesco Del
, p. 979 - 982 (2007/10/02)
Bicyclononan-2-one (1) reacts with methylmagnesium iodide to give, in a high overall yield, a 19:1 mixture of exo-2-methylbicyclononan-2-ol (2) and the endo-epimer (3), respectively.The high propensity of compound (1) for axial attack by a bulky reagent, such as a Grignard reagent, is atypical of bridged cyclohexanones.Possibly, flattening of the bicyclononan-2-one skeleton favours axial attack.Results of the oxymercuriation-demercuriation of related olefins is in accordance with this view.
