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 journalArticle

7 Citations (Scopus)

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.

LanguageEnglish
Pages10588-10591
Number of pages4
JournalChemical Communications
Volume50
Issue number73
Early online date24 Jul 2014
DOIs
Publication statusPublished - 21 Sep 2014

Fingerprint

Alkali Metals
Thermolysis
Alkali metals
Amides
Methane
Salts
Crystalline materials
Derivatives
2,2,6,6-tetramethylpiperidide
phenyllithium
N,N,N',N'-tetramethylethylenediamine

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

Cite this

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. / Dehydromethylation of alkali metal salts of the utility amide 2,2,6,6-tetramethylpiperidide (TMP). In: Chemical Communications. 2014 ; Vol. 50, No. 73. pp. 10588-10591.
@article{1bad65e0924e48c199643982f7268d10,
title = "Dehydromethylation of alkali metal salts of the utility amide 2,2,6,6-tetramethylpiperidide (TMP)",
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",
author = "Kennedy, {Alan R.} and Leenhouts, {Sarah M.} and Liggat, {John J.} and Mart{\'i}nez-Mart{\'i}nez, {Antonio J.} and Kimberley Miller and Mulvey, {Robert E.} and O'Hara, {Charles T.} and Philip O'Keefe and Alan Steven",
year = "2014",
month = "9",
day = "21",
doi = "10.1039/c4cc04959d",
language = "English",
volume = "50",
pages = "10588--10591",
journal = "Chemical Communications",
issn = "1359-7345",
number = "73",

}

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 journalArticle

TY - JOUR

T1 - Dehydromethylation of alkali metal salts of the utility amide 2,2,6,6-tetramethylpiperidide (TMP)

AU - Kennedy, Alan R.

AU - Leenhouts, Sarah M.

AU - Liggat, John J.

AU - Martínez-Martínez, Antonio J.

AU - Miller, Kimberley

AU - Mulvey, Robert E.

AU - O'Hara, Charles T.

AU - O'Keefe, Philip

AU - Steven, Alan

PY - 2014/9/21

Y1 - 2014/9/21

N2 - 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.

AB - 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.

KW - dehydromethylation

KW - alkali metal salts

KW - utility amide

KW - 2,2,6,6-tetramethylpiperidide

KW - general thermolysis reaction

KW - LiTMP

KW - NaTMP

KW - KTMP

KW - group 1 TMP compounds

KW - crystalline complexes

KW - methane elimination

KW - lithium TMP

UR - http://www.scopus.com/inward/record.url?scp=84906228476&partnerID=8YFLogxK

U2 - 10.1039/c4cc04959d

DO - 10.1039/c4cc04959d

M3 - Article

VL - 50

SP - 10588

EP - 10591

JO - Chemical Communications

T2 - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 73

ER -