Facile synthesis of a genuinely alkane-soluble but isolable lithium hydride transfer reagent

Stuart D. Robertson; Alan R. Kennedy; John J. Liggat; Robert E. Mulvey

doi:10.1039/C4CC06421F

Facile synthesis of a genuinely alkane-soluble but isolable lithium hydride transfer reagent

Stuart D. Robertson, Alan R. Kennedy, John J. Liggat, Robert E. Mulvey

Pure And Applied Chemistry

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

33 Citations (Scopus)

118 Downloads (Pure)

Abstract

1-lithio-2-butyl-1,2-dihydropyridines, typically formed as intermediates in the nucleophilic substitution (addition/elimination) of pyridine with (n- or t-) butyl lithium, have been isolated and comprehensively characterized. The linear substituted isomer is polymeric while the branched substituted isomer is a cyclotrimer. The lower oligomerization of the latter complex confers exceptional hexane solubility making it an excellent lithium hydride source in non-polar, aliphatic media.

Original language	English
Pages (from-to)	5452-5455
Number of pages	4
Journal	Chemical Communications
Volume	51
Issue number	25
Early online date	10 Sep 2014
DOIs	https://doi.org/10.1039/C4CC06421F
Publication status	Published - 28 Mar 2015

Keywords

crystallography
isomers
hexane solubility

Access to Document

10.1039/C4CC06421F

Robertson-etal-CC2015-facile-synthesis-alkane-soluble-isolable-lithium-hydrideAccepted author manuscript, 503 KB

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Stuart Robertson
- stuart.d.robertson@strath.ac.uk
- Pure And Applied Chemistry - Senior Lecturer
Person: Academic

3 Finished

A co-operative bimetallic approach for the transformation of lithiation
Mulvey, R.
EPSRC (Engineering and Physical Sciences Research Council)
1/03/13 → 29/02/16
Project: Research
Avenues of application for cooperative bimetallics
Robertson, S.
Royal Society of Edinburgh
1/10/12 → 30/09/17
Project: Research Fellowship
MIXED-METAL MOLECULAR SYNERGY (WOLFSON MERIT AWARD)
Mulvey, R.
Royal Society
1/04/09 → 31/03/14
Project: Research

x-ray diffractometer
Alan Kennedy (Manager)
Pure And Applied Chemistry
Facility/equipment: Equipment

Cite this

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title = "Facile synthesis of a genuinely alkane-soluble but isolable lithium hydride transfer reagent",

abstract = "1-lithio-2-butyl-1,2-dihydropyridines, typically formed as intermediates in the nucleophilic substitution (addition/elimination) of pyridine with (n- or t-) butyl lithium, have been isolated and comprehensively characterized. The linear substituted isomer is polymeric while the branched substituted isomer is a cyclotrimer. The lower oligomerization of the latter complex confers exceptional hexane solubility making it an excellent lithium hydride source in non-polar, aliphatic media.",

keywords = "crystallography, isomers, hexane solubility",

author = "Robertson, {Stuart D.} and Kennedy, {Alan R.} and Liggat, {John J.} and Mulvey, {Robert E.}",

year = "2015",

month = mar,

day = "28",

doi = "10.1039/C4CC06421F",

language = "English",

volume = "51",

pages = "5452--5455",

journal = "Chemical Communications",

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publisher = "Royal Society of Chemistry",

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TY - JOUR

T1 - Facile synthesis of a genuinely alkane-soluble but isolable lithium hydride transfer reagent

AU - Robertson, Stuart D.

AU - Kennedy, Alan R.

AU - Liggat, John J.

AU - Mulvey, Robert E.

PY - 2015/3/28

Y1 - 2015/3/28

N2 - 1-lithio-2-butyl-1,2-dihydropyridines, typically formed as intermediates in the nucleophilic substitution (addition/elimination) of pyridine with (n- or t-) butyl lithium, have been isolated and comprehensively characterized. The linear substituted isomer is polymeric while the branched substituted isomer is a cyclotrimer. The lower oligomerization of the latter complex confers exceptional hexane solubility making it an excellent lithium hydride source in non-polar, aliphatic media.

AB - 1-lithio-2-butyl-1,2-dihydropyridines, typically formed as intermediates in the nucleophilic substitution (addition/elimination) of pyridine with (n- or t-) butyl lithium, have been isolated and comprehensively characterized. The linear substituted isomer is polymeric while the branched substituted isomer is a cyclotrimer. The lower oligomerization of the latter complex confers exceptional hexane solubility making it an excellent lithium hydride source in non-polar, aliphatic media.

KW - crystallography

KW - isomers

KW - hexane solubility

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UR - http://pubs.rsc.org/en/journals/journalissues/cc

U2 - 10.1039/C4CC06421F

DO - 10.1039/C4CC06421F

M3 - Article

AN - SCOPUS:84925060810

VL - 51

SP - 5452

EP - 5455

JO - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 25

ER -

Facile synthesis of a genuinely alkane-soluble but isolable lithium hydride transfer reagent

Abstract

Keywords

Access to Document

Stuart Robertson

A co-operative bimetallic approach for the transformation of lithiation

Avenues of application for cooperative bimetallics

MIXED-METAL MOLECULAR SYNERGY (WOLFSON MERIT AWARD)

x-ray diffractometer

Cite this