92485-85-3Relevant academic research and scientific papers
REGIOSELECTIVE FUNCTIONALIZATION OF cis-BICYCLOOCTENONE DERIVATIVES. OXYMERCURATION/REDUCTION VERSUS HYDROBORATION/OXIDATION. ACETAL GROUPS AS REGIO- AND STEREOSELECTIVE CONTROL ELEMENTS
Carceller, Elena,Castello, Assumpta,Garcia, M. Lluisa,Moyano, Albert,Serratosa, Felix
, p. 775 - 778 (2007/10/02)
Cyclic acetal groups at the position 8 of the cis-bicyclooctane system may act as regio- and stereoselective control elements, respectively, in hydroboration and oxymercuration reactions.Whereas the regioselectivity observed in hydroborations must be ascribed to homoallylic inductive effects, and leads predominantly to exo, 1,3-bifunctional relationships, the effect of acetal group in oxymercuration is mainly stereoselective due to coordination of mercury acetate with the nonbonding electron pairs of the endo-oxygen atom of the acetal group, and leads predominantly to exo, 1,4-bifunctional relationships.
