Dehydromethylation of alkali metal salts of the utility amide 2,2,6,6-tetramethylpiperidide (TMP)

A general thermolysis reaction for the transformation of Group 1 TMP compounds (LiTMP, NaTMP, KTMP) to 1-aza-allylic TTHP derivatives is reported. TMEDA accelerates the reaction and produces the crystalline complexes [(TMEDA)LiTTHP] and [(TMEDA·NaTTHP)2]. Methane elimination during the transformatio...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2014-09, Vol.50 (73), p.10588-10591
Main Authors: Kennedy, Alan R, Leenhouts, Sarah M, Liggat, John J, Martínez-Martínez, Antonio J, Miller, Kimberley, Mulvey, Robert E, O'Hara, Charles T, O'Keefe, Philip, Steven, Alan
Format: Article
Language:English
Subjects:
Alkali metals
Amides
Amides - chemistry
Coordination Complexes - chemistry
Crystal structure
Crystallography, X-Ray
Derivatives
Metals, Alkali - chemistry
Methane
Methane - chemistry
Molecular Conformation
Piperidines - chemistry
Salts - chemistry
Transformations
Utilities
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Summary:A general thermolysis reaction for the transformation of Group 1 TMP compounds (LiTMP, NaTMP, KTMP) to 1-aza-allylic TTHP derivatives is reported. TMEDA accelerates the reaction and produces the crystalline complexes [(TMEDA)LiTTHP] and [(TMEDA·NaTTHP)2]. Methane elimination during the transformational process was confirmed via TVA coupled to MS.
ISSN:1359-7345
1364-548X
DOI:10.1039/c4cc04959d