Reação da cânfora com boroidreto de sódio: uma estratégia para o estudo da estereoquímica da reação de redução

Abstract

REACTION OF CAMPHOR WITH SODIUM BOROHYDRIDE: A STRATEGY TO INTRODUCE THE STEREOCHEMICAL ISSUES OF A REDUCTION REACTION. Reduction of camphor to a mixture of borneol and isoborneol was performed using NaBH4 as the reducing agent under suitable conditions. Although more effective reduction was accomplished using toxic methanol, an alternative non-toxic ethanolic system is described. This experiment is important to introduce undergraduate students in reductive procedures, and can be used to show details on stereoselective procedures on carbonyl moieties (facial diastereoselectivity, Bürgi- Dunitz trajectory, diastereomeric excess).