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Lithium tetramethylpiperidide information


Lithium tetramethylpiperidide
Structural formula of lithium tetramethylpiperidide
Names
IUPAC name
Lithium tetramethylpiperidide
Systematic IUPAC name
1-Lithio-2,2,6,6-tetramethylpiperidine
Identifiers
CAS Number
  • 38227-87-1 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
  • Cyclic tetramer: Interactive image
ChemSpider
  • 21428984 checkY
ECHA InfoCard 100.209.926 Edit this at Wikidata
PubChem CID
  • 11051814
CompTox Dashboard (EPA)
  • DTXSID00453330 Edit this at Wikidata
InChI
  • InChI=1S/C9H18N.Li/c1-8(2)6-5-7-9(3,4)10-8;/h5-7H2,1-4H3;/q-1;+1 checkY
    Key: ANYSGBYRTLOUPO-UHFFFAOYSA-N checkY
SMILES
  • [Li]N1C(C)(C)CCCC1(C)C
  • CC1(C)CCCC(C)(C)N1[Li]
  • Cyclic tetramer: CC1(C)CCCC(C)(C)[N+]01[Li-][N+]1(C(C)(C)CCCC1(C)C)[Li-][N+]1(C(C)(C)CCCC1(C)C)[Li-][N+]1([Li-]0)C(C)(C)CCCC1(C)C
Properties
Chemical formula
 LiC9H18N
Molar mass 147.19 g·mol−1
Acidity (pKa) 37
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Lithium tetramethylpiperidide (often abbreviated LiTMP or LTMP) is a chemical compound with the molecular formula LiC9H18N. It is used as a non-nucleophilic base, being comparable to LiHMDS in terms of steric hindrance.

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Lithium tetramethylpiperidide

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Lithium tetramethylpiperidide (often abbreviated LiTMP or LTMP) is a chemical compound with the molecular formula LiC9H18N. It is used as a non-nucleophilic...

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chemical lithium amide itself as the parent structure. Common lithium amides include lithium diisopropylamide (LDA), lithium tetramethylpiperidide (LiTMP)...

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Lithium diisopropylamide

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nucleophile under certain conditions. Lithium amide Lithium bis(trimethylsilyl)amide (LiHMDS) Lithium tetramethylpiperidide (LiTMP) Evans pKa Table Hamell,...

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Chan rearrangement

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deprotonated by strong non-nucleophilic bases such as lithium tetramethylpiperidide or lithium diisopropylamide (LDA) as in an aldol reaction. The thus...

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Holton Taxol total synthesis

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This was achieved through a Chan rearrangement of 15 using lithium tetramethylpiperidide to give α-hydroxylactone 16 in 90% yield. The hydroxyl group...

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Persistent carbene

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salt with the generation of isobutene: Lithium amides like the diisopropylamide (LDA) and the (tetramethylpiperidide (LiTMP)) generally work well for the...

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