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

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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.
LanguageEnglish
Pages5452-5455
Number of pages4
JournalChemical Communications
Volume51
Issue number25
Early online date10 Sep 2014
DOIs
Publication statusPublished - 28 Mar 2015

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Alkanes
Lithium
Hydrides
Isomers
Paraffins
Dihydropyridines
Oligomerization
Hexanes
Hexane
Pyridine
Substitution reactions
Solubility
pyridine

Keywords

  • crystallography
  • isomers
  • hexane solubility

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.}",
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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

VL - 51

SP - 5452

EP - 5455

JO - Chemical Communications

T2 - Chemical Communications

JF - Chemical Communications

SN - 1359-7345

IS - 25

ER -