124658-21-5Relevant academic research and scientific papers
N-FLUORO-O-BENZENEDISULFONIMIDE: A USEFUL NEW FLUORINATING REAGENT
Davis, Franklin A.,Han, Wei
, p. 1631 - 1634 (1991)
N-Fluoro-o-benzenedisulfonimide (5) is a stable, easily prepared, highly efficient source of "electrophilic" fluorine which fluorinates enolates, azaenolates and carbanions in good to excellent yields.
Effect of fluorine substitution of α-and β-hydrogen atoms in ethyl phenylacetate and phenylpropionate on their stereoselective hydrolysis by cultured cancer cells
Yamazaki, Yoshimitsu,Yusa, Shiro,Kageyama, Yu-Ichi,Tsue, Hirohito,Hirao, Ken-Ichi,Okuno, Hiroaki
, p. 167 - 171 (2007/10/03)
(±)-Ethyl 2-fluoro-2-phenylacetate was stereoselectively hydrolyzed by cultured cells of several rat cancer cell lines to give the carboxylic acid rich in the R enantiomer. The stereoselectivity increased for (±)-ethyl 2-fluoro-2-phenylpropionate (2b) with all present cell lines and for (±)-ethyl 2-phenyl-3,3,3-trifluoropropionate (3b) with rat hepatoma McA-RH7777 cell line. The stereoselectivity was different for the different cell lines, as McA-RH7777 cells preferred (R)-2b in contrast with the preference towards (S)-2b by other cells such as ras oncogene-transformed rat liver Anr4 cells. These stereoselectivities were different from those for non-fluorinated (±)-ethyl 2-phenylpropionate. Thus fluorine atoms are recognized by ester hydrolases of cancer cells, and fluorine substitution on the acyl group will be useful for making ester-type anticancer prodrugs more specific to cancer cells.
Synthesis of 2-fluoro- acids, esters, and amides from α-dicyanoepoxides
Amanetoullah, A. Ould,Chaabouni,Baklouti
, p. 1155 - 1161 (2007/10/03)
The opening of α-dicyanoepoxides by pyridine polyhydrofluoride yields polymerisable 2-fluorocyanoformyls which may be kept intact when diluated in dichloromethane or ether. These intermediates react with nucleophiles such as water, methanol or amines to give respectively 2-fluoroacids, esters or amides.
Selective, Electrophilic Fluorinations Using N-Fluoro-o-benzenedisulfonimide
Davis, Franklin A.,Han, Wei,Murphy, Christopher K.
, p. 4730 - 4737 (2007/10/02)
The synthesis of N-fluoro-o-benzenedisulfonimide (NFOBS, 2) and its use as an "electrophilic" fluorinating reagent with nucleophilic substrates is described and compared with that of N-fluorobenzenesulfonimide (NFSi, 3).NFOBS (2) is prepared in three steps in 81percent overall yield from commercially available o-benzenedisulfonic acid (4) and involves treatment of o-benzenedisulfonimide (6) with dilute fluorine (10percent F2/N2).Reaction of 2 with metal enolates, silyl enol ethers, and 1,3-dicarbonyl compounds affords the corresponding α-fluoro compounds in yields up to 95percent, with good control of mono- and difluorination.Fluorination of ortho-metalated aromatic compounds was achieved in modest to good yields (10-80percent).While the reactivities of 2 and 3 are similar, better yields were observed with the former reagent in the fluorination of metal enolates, Grignard and lithium reagents, while 3 gave better results with the ortho-lithiated aromatic substrates.The available evidence suggests an SN2-type mechanism for the fluorination of nucleophilic substrates by these reagents.
Acide 2-fluoro-2-phenyl propanoique: preparation et utilisation comme agent chiral de derivation
Hamman, S.
, p. 225 - 232 (2007/10/02)
The enantiomers of 2-fluoro-2-phenyl propanoic acid have been separated and their absolute configurations determined: the specific rotation of the acid with an R configuration is 20D= -28.5 deg (c=1.5, ethanol).This acid has been
N-fluorinated sulfonamides
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, (2008/06/13)
Compounds of formula I STR1 wherein R1, R2, R3 and R4 are H, alkyl or aryl, m and n are 0 or 1, and A is a divalent organic radical which, with (CR1 R2)m NF--SO2 (CR3 R4)n groups, forms a 5- to 8-membered ring, are admirably suitable fluorinating agents for fluorinating carbon atoms, especially as stereospecific fluorinating agents, when the compounds contain a chiral carbon atom and are in optically active form. The compounds of formula I are prepared by reacting the corresponding silated sulfonamides, wherein the NF group is replaced by an N-SiR7 R8 R9 group and R7, R8 R9 are each independently C1 -C12 alkyl, cyclopentyl, cyclohexyl, benzyl or phenyl, with a fluorinating agent.
FLUORINATED HETEROCYCLES: TARGETS IN THE SEARCH FOR BIOACTIVE COMPOUNDS AND TOOLS FOR THEIR PREPARATION
Differding, E.,Frick, W.,Lang, R. W.,Martin, P.,Schmit, C.,et al.
, p. 647 - 671 (2007/10/02)
To strategies for the preparation and use of fluorinated heterocycles are discussed: 1.)the building block approach being used mainly for the preparation of target heterocycles with fluorinated substituents, and 2.)the direct fluorination approach in which fluorinated heterocycles are used as tools for the preparation of bioactive compounds.Strategies presented in the building block approach include electrophilic reactions of building blocks derived from trifluoroacetic acid (1), as well as the use of building blocks obtained from trichlorotrifluoroethane (2) and chlorodifluoro acetic acid (3) through organometallic reactions.The preparation and use of N-fluoro sultams 62 and 66 are shown in the direct fluorination approach.Both strategies can be successfully used n the synthesis of bioactive compounds of pharmaceutical and agrochemical interest.
New Fluorinating Reagents. Part II. Preparation and Synthetic Application of a Saccharin Derived N-Fluorosultam
Differding, Edmond,Lang, Robert W.
, p. 1248 - 1252 (2007/10/02)
The synthesis of the new saccharin derived N-fluorosultam 1 is described.A comparative study with commercially available N-fluorosulfonamides shows 1 to be a superior fluorinating reagent for the synthesis of α-fluorocarbonyl compounds.
