Sixty years after Wittig: Gas-phase synthesis of lithium trimethyl-ammonium methylide, [(CH3)3NCH2Li]

Richard A.J. O'Hair; Tom Waters; Benjamin Cao

doi:10.1002/anie.200701972

Sixty years after Wittig: Gas-phase synthesis of lithium trimethyl-ammonium methylide, [(CH₃)₃NCH₂Li]

Richard A.J. O'Hair, Tom Waters, Benjamin Cao

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

26 Citations (Scopus)

Abstract

(Graph Presented) Very Wittig: Collisional activation of the lithiated betaine cation [(CH₃)₃NCH₂CO ₂Li]⁺ (m/z 124) in the gas phase results in decarboxylation to form the lithiated ylide [(CH₃) ₃NCH₂Li]⁺ (m/z 80). Calculations and ion-molecule reactions with water confirm the identity and reactivity of this species.

Original language	English
Pages (from-to)	7048-7051
Number of pages	4
Journal	Angewandte Chemie - International Edition
Volume	46
Issue number	37
DOIs	https://doi.org/10.1002/anie.200701972
Publication status	Published - 17 Sept 2007
Externally published	Yes

Keywords

Betaines
Carbanions
Density functional calculations
Ion-molecule reactions
Ylides

Access to Document

10.1002/anie.200701972

Cite this

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title = "Sixty years after Wittig: Gas-phase synthesis of lithium trimethyl-ammonium methylide, [(CH3)3NCH2Li]",

abstract = "(Graph Presented) Very Wittig: Collisional activation of the lithiated betaine cation [(CH3)3NCH2CO 2Li]+ (m/z 124) in the gas phase results in decarboxylation to form the lithiated ylide [(CH3) 3NCH2Li]+ (m/z 80). Calculations and ion-molecule reactions with water confirm the identity and reactivity of this species.",

keywords = "Betaines, Carbanions, Density functional calculations, Ion-molecule reactions, Ylides",

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T1 - Sixty years after Wittig

T2 - Gas-phase synthesis of lithium trimethyl-ammonium methylide, [(CH3)3NCH2Li]

AU - O'Hair, Richard A.J.

AU - Waters, Tom

AU - Cao, Benjamin

PY - 2007/9/17

Y1 - 2007/9/17

N2 - (Graph Presented) Very Wittig: Collisional activation of the lithiated betaine cation [(CH3)3NCH2CO 2Li]+ (m/z 124) in the gas phase results in decarboxylation to form the lithiated ylide [(CH3) 3NCH2Li]+ (m/z 80). Calculations and ion-molecule reactions with water confirm the identity and reactivity of this species.

AB - (Graph Presented) Very Wittig: Collisional activation of the lithiated betaine cation [(CH3)3NCH2CO 2Li]+ (m/z 124) in the gas phase results in decarboxylation to form the lithiated ylide [(CH3) 3NCH2Li]+ (m/z 80). Calculations and ion-molecule reactions with water confirm the identity and reactivity of this species.

KW - Betaines

KW - Carbanions

KW - Density functional calculations

KW - Ion-molecule reactions

KW - Ylides

UR - https://www.scopus.com/pages/publications/34848881880

U2 - 10.1002/anie.200701972

DO - 10.1002/anie.200701972

M3 - Article

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JO - Angewandte Chemie - International Edition

JF - Angewandte Chemie - International Edition

IS - 37