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A Study of BF3‐Promoted ortho Lithiation of Anilines and DFT Calculations on the Role of Fluorine–Lithium Interactions

Identifieur interne : 001055 ( Main/Exploration ); précédent : 001054; suivant : 001056

A Study of BF3‐Promoted ortho Lithiation of Anilines and DFT Calculations on the Role of Fluorine–Lithium Interactions

Auteurs : Satinder Kessar [Inde] ; Paramjit Singh ; Kamal Singh ; Prasad Bharatam ; Arvind Sharma ; Sneh Lata ; Amarjit Kaur

Source :

RBID : ISTEX:01557950918386849AB839365C861F3E77833819

English descriptors

Abstract

Überraschende Hilfe: Aus der bei der ortho‐Metallierung kaum steuernd wirkenden Dimethylaminogruppe wird durch die Komplexierung mit BF3 eine stärker als Methoxy‐ und Chlorgruppen aktivierende Gruppe. Nach DFT‐Rechnungen an vereinfachten lithiierten Intermediaten spielt der induktive Effekt kaum eine Rolle, während eine deutliche F⋅⋅⋅Li‐Wechselwirkung zu einem F‐Li‐Abstand führt, der dem C‐Li‐Abstand erstaunlich nahekommt.

Url:
DOI: 10.1002/ange.200705967


Affiliations:


Links toward previous steps (curation, corpus...)


Le document en format XML

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<div type="abstract">Überraschende Hilfe: Aus der bei der ortho‐Metallierung kaum steuernd wirkenden Dimethylaminogruppe wird durch die Komplexierung mit BF3 eine stärker als Methoxy‐ und Chlorgruppen aktivierende Gruppe. Nach DFT‐Rechnungen an vereinfachten lithiierten Intermediaten spielt der induktive Effekt kaum eine Rolle, während eine deutliche F⋅⋅⋅Li‐Wechselwirkung zu einem F‐Li‐Abstand führt, der dem C‐Li‐Abstand erstaunlich nahekommt.</div>
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