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

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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.