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2,2,6,6-Tetramethylpiperidine is a hindered base used to prepare metallo-amide bases and selective generation of silylketene acetals. It is used in the preparation of hibarimicinone, (Z)-silylketene acetal and 4-substituted quinazoline. It acts as a precursor to Lithium tetramethylpiperidide and (2,2,6,6-Tetramethylpiperidin-1-yl)oxyl radical.
Lithiation gives a highly-hindered, non-nucleophilic strong base; see, e.g. Org. Synth. Coll., 6, 571 (1988); 9, 426 (1998); Tetrahedron, 50, 3099 (1994). For use in selective isomerization of epoxides to aldehydes, see: J. Chem. Soc., Chem. Commun., 2103 (1994). For a study of the influence of TMEDA and related chelating ligands on the solution structure of the lithiated base, see: J. Org. Chem., 62, 5748 (1997). The Mg derivative, obtained by reaction with n-BuMgCl, is also an effective strong base which has been used in the regioselective ortho-metallation of pyridine carbamates and carboxamides: J. Org. Chem., 60, 8414 (1995).
Walker, W. K.; Kay, B. M.; Michaelis, S. A.; Anderson, D. L.; Smith, S. J.; Ess, D. H.; Michaelis, D. J. Origin of Fast Catalysis in Allylic Amination Reactions Catalyzed by Pd-Ti Heterobimetallic Complexes. J. Am. Chem. Soc. 2015, 137 (23), 7371-7378.
Longobardi, L. E.; Mahdi, T.; Stephan, D. W. B(C6F5)3 mediated arene hydrogenation/transannulation of para-methoxyanilines. Dalton Trans. 2015, 44 (16), 7114-7117.
Hazard Statements: H226-H302-H314-H318
Flammable liquid and vapour. Harmful if swallowed. Causes severe skin burns and eye damage. Causes serious eye damage.
Precautionary Statements: P280-P305+P351+P338-P309-P310a
Wear protective gloves/protective clothing/eye protection/face protection. IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. IF exposed or if you feel unwell: Immediately call a POISON CENTER/doctor