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In the same year, Stahly described similar reactions for the synthesis of trifluoromethylated phenols and anilines. [13] Since then TMSCF 3 has been widely used as a nucleophilic trifluoromethylating agent. [14] [15] An example is the trifluoromethylation of cyclohexanone in THF using tetrabutylammonium fluoride. [16]
3-(Trifluoromethyl)aniline is an organic compound with the formula CF 3 C 6 H 4 NH 2. It is one of three isomers of trifluoromethylaniline. It is one of three isomers of trifluoromethylaniline. Classified as an aromatic amines , they are colorless liquids.
Trifluoromethyl group covalently bonded to an R group. The trifluoromethyl group is a functional group that has the formula-CF 3.The naming of is group is derived from the methyl group (which has the formula -CH 3), by replacing each hydrogen atom by a fluorine atom.
4-Fluoroaniline can be prepared by the hydrogenation of 4-nitrofluorobenzene. [2] It is a common building block in medicinal chemistry and related fields. [3] For example, it is a precursor to the fungicide fluoroimide or the fentanyl analogue parafluorofentanyl. It has also been evaluated for the production of ligands for homogeneous catalysis ...
It is unclear why trifluralin's exotic 4-trifluoromethyl was tested so early (1960), before more common candidates such as fluoro, bromo, or iodo. [7] By 1968, trifluralin was internationally available, including Australia and New Zealand, [6] and trifluralin was the 5th most used herbicide in the US, at 22,960,000 pounds (10,410 t) by 1974. [11]
[2] [3] It is highly electrophilic and fluoral forms a hydrate CF 3 CH(OH) 2 upon contact with water like other halogenated acetaldehydes. [4] It is commonly used in form of ethyl hemiacetal (1-ethoxy-2,2,2-trifluoroethanol, CF 3 CH(OCH 2 CH 3 )(OH) ) due to the aldehyde's high reactivity, including the tendency to polymerise.
Typically these reactions would be conducted in the presence of a base which serves to absorb the HCl. Alkyl chloroformate esters degrate to give the alkyl chloride, with retention of configuration: ROC(O)Cl ' → RCl + CO 2. The reaction is proposed to proceed via a substitution nucleophilic internal mechanism. [3]
A related popular catalyst scandium triflate is used in such reactions as aldol reactions and Diels–Alder reactions. An example is the Mukaiyama aldol addition reaction between benzaldehyde and the silyl enol ether of cyclohexanone with an 81% chemical yield. [2] The corresponding reaction with the yttrium salt fails: Sc(OTf) 3-mediated aldol ...