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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Intramolecular sila-Matteson rearrangement: a general access to silylated heterocycles
Cyril François1, Thomas Boddaert, Muriel Durandetti
1CNRS UMR 6014 COBRA & FR 3038 INC3M, Université de Rouen and INSA de Rouen, 76821 Mont St. Aignan Cedex, France.
Abstract:
A series of new silylated heterocycles has been efficiently prepared using an intramolecular silicon version of the Matteson rearrangement, providing two isomers of binuclear heterocycles. This method applies to a large variety of substrates, a direct relationship between the Hammett constants of the aromatic substituents and the isomer ratio being observed. Complementary experiments suggest that a common pentaorganosilicate species is involved.
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