Hydration of endo-Tricyclo[5,2,1,02,6]deca-3,8-diene (endo-Dicyclopentadiene) / Über die Hydratisierung von endo-Tricyclo[5.2.1.02,6]deca-3.8-dien (endo-Dicyclopentadien)

Abstract

The hydration of endo-dicyclopentadiene (1) yields a 1:2 mixture of exo-8-hydroxy-exotricyclo[5,2,1,02,6]dec-3-ene (2) and exo-9-hydroxy-exo-tricyclo[5,2,1,02,6]dec-3-ene (3). The structures of these compounds were determined by 1H and 13C spectroscopy with simultaneous application of paramagnetic shift reagent Eu(fod)3. The stereospecific exoattack of the proton in the first reaction step is demonstrated by the reaction in deuteriumoxid.