Issue 73, 2014
From the journal:

Chemical Communications

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

Alan R. Kennedy,a   Sarah M. Leenhouts,a   John J. Liggat,a   Antonio J. Martínez-Martínez,a   Kimberley Miller,a   Robert E. Mulvey,*a   Charles T. O'Hara,*a   Philip O'Keefeb  and  Alan Stevenb  

* Corresponding authors

a WestCHEM, Department of Pure and Applied Chemistry, University of Strathclyde, Glasgow, UK
E-mail: r.e.mulvey@strath.ac.uk, charlie.ohara@strath.ac.uk

b Chemical Development, AstraZeneca, Silk Road Business Park, Charter Way, Macclesfield, UK

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.

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

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Article information

DOI
https://doi.org/10.1039/C4CC04959D
Article type
Communication
Submitted
29 Jun 2014
Accepted
23 Jul 2014
First published
24 Jul 2014

Chem. Commun., 2014,50, 10588-10591

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

A. R. Kennedy, S. M. Leenhouts, J. J. Liggat, A. J. Martínez-Martínez, K. Miller, R. E. Mulvey, C. T. O'Hara, P. O'Keefe and A. Steven, Chem. Commun., 2014, 50, 10588 DOI: 10.1039/C4CC04959D

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