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

Alan R. Kennedy; Sarah M. Leenhouts; John J. Liggat; Antonio J. Martínez-Martínez; Kimberley Miller; Robert E. Mulvey; Charles T. O'Hara; Philip O'Keefe; Alan Steven

doi:10.1039/c4cc04959d

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

Alan R. Kennedy, Sarah M. Leenhouts, John J. Liggat, Antonio J. Martínez-Martínez, Kimberley Miller, Robert E. Mulvey, Charles T. O'Hara, Philip O'Keefe, Alan Steven

Research output: Contribution to journal › Article

8 Citations (Scopus)

203 Downloads (Pure)

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.

Original language	English
Pages (from-to)	10588-10591
Number of pages	4
Journal	Chemical Communications
Volume	50
Issue number	73
Early online date	24 Jul 2014
DOIs	https://doi.org/10.1039/c4cc04959d
Publication status	Published - 21 Sep 2014

Keywords

dehydromethylation
alkali metal salts
utility amide
2,2,6,6-tetramethylpiperidide
general thermolysis reaction
LiTMP
NaTMP
KTMP
group 1 TMP compounds
crystalline complexes
methane elimination
lithium TMP

Access to Document

10.1039/c4cc04959d

Revised TMP Dehydromethylation ChemCommAccepted author manuscript, 4.86 MBLicence: CC BY-NC-SA 4.0

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Kennedy, A. R., Leenhouts, S. M., Liggat, J. J., Martínez-Martínez, A. J., Miller, K., Mulvey, R. E., ... Steven, A. (2014). Dehydromethylation of alkali metal salts of the utility amide 2,2,6,6-tetramethylpiperidide (TMP). Chemical Communications, 50(73), 10588-10591. 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.",

keywords = "dehydromethylation, alkali metal salts, utility amide, 2,2,6,6-tetramethylpiperidide, general thermolysis reaction, LiTMP , NaTMP, KTMP, group 1 TMP compounds, crystalline complexes, methane elimination, lithium TMP",

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

In: Chemical Communications, Vol. 50, No. 73, 21.09.2014, p. 10588-10591.

Research output: Contribution to journal › Article

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AU - Leenhouts, Sarah M.

AU - Liggat, John J.

AU - Martínez-Martínez, Antonio J.

AU - Miller, Kimberley

AU - Mulvey, Robert E.

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AU - O'Keefe, Philip

AU - Steven, Alan

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