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research article

Rate enhancing and rate retarding effects of methoxy substituents on arene metalation

Maggi, Raimondo
•
Schlosser, Manfred  
1999
Tetrahedron Letters

Competition expts. have been performed to det. the rates, relative to benzene, with which anisole, the three dimethoxybenzenes and the three trimethoxybenzenes are deprotonated by sec-butyllithium. Only the first substituent (anisole relative to benzene) has a strong effect (krelf 2800); the second one accelerates moderately at best (1,3-dimethoxybenzene relative to anisole: krelf 12). Methoxy groups being located para with respect to the metalation site or occupying a vicinal position to another methoxy substituent diminish the reactivity by up to two powers of ten (relative to anisole). These surprising findings are without precedence. [on SciFinder (R)]

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Type
research article
DOI
10.1016/S0040-4039(99)01872-9
Author(s)
Maggi, Raimondo
Schlosser, Manfred  
Date Issued

1999

Publisher

Elsevier

Published in
Tetrahedron Letters
Volume

40

Issue

50

Start page

8797

End page

8800

Subjects

Lithiation; Lithiation (kinetics; rate enhancing and rate retarding effects of methoxy substituents on arene metalation); Metalation kinetics; Metalation kinetics (lithiation kinetics; rate enhancing and rate retarding effects of methoxy substituents on

•

methoxy substituent effect arene metalation; deprotonation benzene relative kinetics methoxy substituent effect

Note

CAN 132:92998

22-12

Physical Organic Chemistry

Institut de Chimie organique de l'Universite (BCh),Lausanne,Switz.

Journal

written in English.

71-43-2 (Benzene); 91-16-7 (Catechol dimethyl ether); 100-66-3 (Anisole); 135-77-3 (Hydroxyhydroquinone trimethyl ether); 150-78-7 (Hydroquinone dimethyl ether); 151-10-0 (Resorcinol dimethyl ether); 621-23-8; 634-36-6 (Pyrogallol trimethyl ether) Role: PRP (Properties), RCT (Reactant), RACT (Reactant or reagent) (rate enhancing and rate retarding effects of methoxy substituents on arene metalation)

Editorial or Peer reviewed

REVIEWED

Written at

EPFL

EPFL units
LSCO  
Available on Infoscience
March 3, 2006
Use this identifier to reference this record
https://infoscience.epfl.ch/handle/20.500.14299/226965
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