Publication

Fluorine and trifluoromethyl substituted anilines: site selective metalation and electrophilic substitution

Manfred Schlosser
1992
Journal Articles

Abstract

When treated with tert-butyllithium in THF at -50 Deg, N-BOC (tert-butoxycarbonyl) protected fluoroanilines and trifluoromethylanilines, e.g., o-, m-, or p-F3CC6H4NHCO2CMe3, undergo metalation at the position adjacent to that carrying the nitrogen. If, however, the nitrogen carries two alkyl or trimethylsilyl groups as substituents and highly polar metalating reagents such as butyllithium activated by N,N,N',N",N"-pentamethyldiethylenetriamine (PMDTA) or potassium tert-butoxide are employed, the fluoroaniline derivs. are preferentially deprotonated next to the halogen atom. [on SciFinder (R)]

Official source

https://infoscience.epfl.ch/entities/publication/676f62c6-53ed-4f05-b94c-1024a681344a

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Manfred Schlosser
1992
Journal Articles

Abstract

Official source

https://infoscience.epfl.ch/entities/publication/676f62c6-53ed-4f05-b94c-1024a681344a

About this result

Related concepts (20)

Organolithium reagent

In organometallic chemistry, organolithium reagents are chemical compounds that contain carbon–lithium (C–Li) bonds. These reagents are important in organic synthesis, and are frequently used to transfer the organic group or the lithium atom to the substrates in synthetic steps, through nucleophilic addition or simple deprotonation. Organolithium reagents are used in industry as an initiator for anionic polymerization, which leads to the production of various elastomers.

Halogen

The halogens (ˈhælədʒən,ˈheɪ-,-loʊ-,_-ˌdʒɛn) are a group in the periodic table consisting of six chemically related elements: fluorine (F), chlorine (Cl), bromine (Br), iodine (I), astatine (At), and tennessine (Ts), though some authors would exclude tennessine as its chemistry is unknown and is theoretically expected to be more like that of gallium. In the modern IUPAC nomenclature, this group is known as group (XVII) or group (VII). The word "halogen" means "salt former" or "salt maker".

Tert-Butyllithium

tert-Butyllithium is a chemical compound with the formula (CH3)3CLi. As an organolithium compound, it has applications in organic synthesis since it is a strong base, capable of deprotonating many carbon molecules, including benzene. tert-Butyllithium is available commercially as hydrocarbon solutions; it is not usually prepared in the laboratory. tert-Butyllithium is produced commercially by treating tert-butyl chloride with lithium metal. Its synthesis was first reported by R. B. Woodward in 1941.