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

Kennedy, Alan R. and Leenhouts, Sarah M. and Liggat, John J. and Martínez-Martínez, Antonio J. and Miller, Kimberley and Mulvey, Robert E. and O'Hara, Charles T. and O'Keefe, Philip and Steven, Alan (2014) Dehydromethylation of alkali metal salts of the utility amide 2,2,6,6-tetramethylpiperidide (TMP). Chemical Communications, 50 (73). pp. 10588-10591. ISSN 1359-7345 (https://doi.org/10.1039/c4cc04959d)

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Abstract

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.

ORCID iDs

Kennedy, Alan R. ORCID logoORCID: https://orcid.org/0000-0003-3652-6015, Leenhouts, Sarah M., Liggat, John J. ORCID logoORCID: https://orcid.org/0000-0003-4460-5178, Martínez-Martínez, Antonio J., Miller, Kimberley, Mulvey, Robert E. ORCID logoORCID: https://orcid.org/0000-0002-1015-2564, O'Hara, Charles T., O'Keefe, Philip and Steven, Alan;
CORE (COnnecting REpositories)