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

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

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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.

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 Sept 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

Cite this

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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 = sep,

day = "21",

doi = "10.1039/c4cc04959d",

language = "English",

volume = "50",

pages = "10588--10591",

journal = "Chemical Communications",

issn = "1359-7345",

publisher = "Royal Society of Chemistry",

number = "73",

}

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

AN - SCOPUS:84906228476

SN - 1359-7345

VL - 50

SP - 10588

EP - 10591

JO - Chemical Communications

JF - Chemical Communications

IS - 73

ER -

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

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John Liggat

Lithium Cuprates to Copper Lithiates: A New Dawn in Metal Catalysed Chemistry

A co-operative bimetallic approach for the transformation of lithiation

Chiral Concepts in s-Block Metal Amide Chemistry

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

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

Abstract

Keywords

Access to Document

Other files and links

Fingerprint

Profiles

John Liggat

Projects

Lithium Cuprates to Copper Lithiates: A New Dawn in Metal Catalysed Chemistry

A co-operative bimetallic approach for the transformation of lithiation

Chiral Concepts in s-Block Metal Amide Chemistry

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

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