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  4. Site selective hydrogen/metal exchange: competition and cooperation between superbases and neighboring groups
 
research article

Site selective hydrogen/metal exchange: competition and cooperation between superbases and neighboring groups

Schlosser, Manfred  
•
Faigl, Ferenc
•
Franzini, Livia
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1994
Pure and Applied Chemistry

A review with 62 refs. The appropriate choice of a metalating reagent is the key to the optional deprotonation of benzylamine derivs. at a position adjacent to the substituent or the nitrogen bearing side chain or even at the benzylic a-position of the latter. Subsequent reaction with suitable electrophiles followed by cyclization affords heterocyclic products such as isoquinolines and isoindolones. Immediately when generated, some organometallic intermediates can undergo a rapid second hydrogen/metal exchange process. However, demetalation is only kinetically, not thermodn. favored as a careful investigation of typical cases has revealed. Moreover, it can be avoided if the donor capacity of the solvent or the polarity of the metalating reagent is increased. Allylic organopotassium compds. exhibit intriguing stereopreferences. This peculiarity has been exploited in a no. of very simple sesquiterpene syntheses. [on SciFinder (R)]

  • Details
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Type
research article
Author(s)
Schlosser, Manfred  
Faigl, Ferenc
Franzini, Livia
Geneste, Herve
Katsoulos, Georges
Zhong, Guo Fu
Date Issued

1994

Published in
Pure and Applied Chemistry
Volume

66

Issue

7

Start page

1439

End page

46

Subjects

Protonation and Proton transfer reaction (deprotonation

•

site selective hydrogen/metal exchange

•

in org. synthesis); Synthesis (org.

•

site selective hydrogen/metal exchange and)

•

review deprotonation org synthesis

Note

CAN 121:82077 21-0 General Organic Chemistry Institut Chimie Organique,Universite Lausanne,Lausanne,Switz. Journal; General Review 0033-4545 written in English. 12408-02-5 Role: RCT (Reactant), RACT (Reactant or reagent) (protonation and Proton transfer reaction, deprotonation, site selective hydrogen/metal exchange, in org. synthesis)

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/20.500.14299/226910
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