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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Complementarity of solution and solid state mechanochemical reaction conditions demonstrated by 1,2-debromination of
Petar Štrbac1, Davor Margetić1
1Ruđer Bošković Institute, Bijenička cesta 54, HR-10002 Zagreb, Croatia.
Abstract:
The solution phase 1,2-debromination of polycyclic imides using the Zn/Ag couple was successfully transferred to solid state mechanochemical conditions. The Zn/Ag couple was replaced by the Zn/Cu couple which was prepared without any metal activation by in situ ball milling of zinc and copper dusts. The advantage of the ball milling process is that the whole procedure is operationally very simplified. The reactive alkene generated was trapped in situ by several dienes and the respective Diels-Alder cycloadducts were obtained. It was demonstrated that mechanochemical milling offers complementary conditions to solution (thermal) reaction by allowing chemical transformations to proceed which were not possible in solution and vice versa.
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