6461-76-3Relevant articles and documents
A new effective synthesis of arene mono- and disulfonyl chlorides
Barbero, Margherita,Bazzi, Stefano,Cadamuro, Silvano,Dughera, Stefano,Magistris, Claudio,Venturello, Paolo
supporting information; experimental part, p. 1803 - 1806 (2010/10/20)
Arene mono- and disulfonyl chlorides have been easily synthesized starting from the corresponding anilines via aqueous oxidative chlorination of S-aryl O-ethyl dithiocarbonates intermediates, aryl methyl sulfides, or from arenethiols. Georg Thieme Verlag Stuttgart.
N,N-1,2-benzenedisulfonylimide, a new cyclic leaving group for the stereoselective nucleophilic substitution of amines
Sorbye, Karsten,Tautermann, Christoffer,Carlsen, Per,Fiksdahl, Anne
, p. 681 - 689 (2007/10/03)
We hereby report the preparation and nucleophilic substitutions of the N,N-1,2-benzenedisulfonylimide derivatives la and 2a of the chiral amines 1 and 2. The nucleophilic attack of KNO2 afforded the respective alcohols 3 and 4 with 84-90% inversion of configuration. Nucleophilic attack by the azide ion afforded the azide products 5 and 6 which were reduced to the corresponding inverted mines 1 and 2 (94-98.5% inversion). The improved leaving group ability of the N,N-1,2-benzenedisulfonylimides compared with previously reported N,N-disulfonylimides is discussed. Chiral GLC analysis of all products is summarized and the alternative chiral analysis of product 3 by 13C NMR using heptakis(2,3,6-tri-O-methyl)-β-cyclodextrin as a chiral solvating agent (CSA) is discussed.
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.
A SIMPLE SYNTHESIS AND SOME CHEMICAL PROPERTIES OF BENZO-1,4-DITHIAFULVENES
Barbero, Margherita,Cadamuro, Silvano,Ceruti, Maurizio,Degani, Iacapo,Fochi, Rita,Regondi, Valeria
, p. 227 - 236 (2007/10/02)
The synthesis of benzo-1,4-dithiafulvenes by a simple treatment of 2-substituted 1,3-benzodithiolium tetrafluoroborates - obtained starting from carboxylic acids or acyl chlorides and tetrafluoroboric acid/ ether complex - with acetonitrile water is reported.The reaction is very fast and affords the products in high over-all yields and under mild conditions.The reactions of benzo-1,4-dithiafulvenes with reducing agents (zinc/trifluoroacetic acid and acetonitrile, zinc/deuterated trifluoroacetic acid and acetonitrile, Raney nickel) and with oxidizing agents (hydrogen peroxide/ acetic acid, sodium hypochlorite, chlorine gas/water) are also reported.These reactions show the interesting synthetic potential of benzo-1,4-dithiafulvenes.
A CONVENIENT SYNTHESIS OF 1,2-BENZENEDISULPHONYL CHLORIDE
Barbero, Margherita,Degani, Iacopo,Fochi, Rita,Regondi, Valeria
, p. 165 - 166 (2007/10/02)
A new method for the synthesis of 1,2-benzenedisulphonyl chloride starting from anthranilic acid, via 2-(3-methylbutoxy)-1,3-benzodithiole or 1,3-benzodithiolium tetrafluroborate is described.
STUDIEN ZUM VORGANG DER WASSERSTOFFUEBERTRAGUNG 62. HERSTELLUNG UND ELEKTROREDUKTIVE SPALTUNG EINIGER ARYLDISULFONSAEUREDERIVATE
Horner, Leopold,Schmitt, Rolf-Elhard
, p. 169 - 178 (2007/10/02)
Benzene-disulfonylchlorides were converted to the corresponding dialkyl- and diphenylesters, N-alkyl- and N-aryl disulfonamides.The half-wave-potentials E11/2 and E21/2 were measured and the products obtained on potentiostatic fission at E11/2 were isolated and characterized.The electroreduction of benzene-1,4-disulfonic acid-diphenylester in methanol yields phenol in quantity approximately corresponding to the current passed, but no corresponding quantity of sulfinic acid.In dry acetonitrile, benzene-1,4-disulfonic acid diesters and diamides undergo potentiostatic fission (at E11/2) in good chemical and current yields, giving the corresponding monosulfonate-sulfinic acid or monosulfonamide-sulfinic acid and alcohol or amine.The passage of further electrical current reduces the sulfinic acids to other, as yet undetermined, products.
