Publication

Fluorine- and trifluoromethyl-substituted toluenes: site selective metalation of aromatic or benzylic positions

Manfred Schlosser
1991
Journal Articles

Abstract

At -75 Deg, the superbasic mixt. of BuLi and KOCMe3 metalates 2-, 3-, and 4-FC6H4Me exclusively at an arom. position adjacent to the halogen, as demonstrated by quenching with CO2 to give the corresponding benzoic acids. In contrast, a mixt. of LiN(CHMe2)2 and KOCMe3 selectively deprotonates the benzylic positions of 2- and 3-FC6H4Me to give after quenching with CO2 the corresponding phenylacetic acids. With 3-(F3C)C6H4Me, metal/hydrogen exchange again occurs at the Me group while the corresponding 2- and 4-isomers do not produce interceptable organometallic intermediates. [on SciFinder (R)]

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https://infoscience.epfl.ch/entities/publication/0298dcea-7e74-4d79-b2ae-65d640a6150e

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Manfred Schlosser
1991
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/0298dcea-7e74-4d79-b2ae-65d640a6150e

About this result

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Fluorine- and trifluoromethyl-substituted toluenes: site selective metalation of aromatic or benzylic positions

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