Mohamed Beji

Synthesis of Highly Fluorinated Aryl N-Acylsulfamates and Evaluation of Their Surfactant Properties

Abstract Reaction of highly fluorinated carboxylic acids with aroxysulfonylisocyanates in the presence of triethylamine allowed the preparation of the corresponding highly fluorinated aroxy-N-sulfonylsulfamates. The reaction proceeds with good yield in toluene at room temperature or more rapidly in the same solvent at 60 °C. Surface tension measurement at the air/water interface showed that these compounds constitute new excellent nonionic surfactants exhibiting high surface activity in the range of the best nonionic fluoro surfactants, already described in the literature. The critical micelle concentration (CMC) has been calculated from the surface tension measurements on surface aqueous solutions. GRAPHICAL ABSTRACT

Alkylation des Esters Sulfamiques par le Bromure de 4-Fluorobenzyle

Abstract The action of 4-fluorobenzyl bromide on sulfamic esters (R-O-SO 2 -NH 2 ) in liquid–liquid phase transfer conditions allows, depending on the nature of R, the preparation of the N-dialkyled products or the corresponding ethers by scission of the O–SO 2 bond.

Reaction of Acids and Diacids with Aroxy(alcoxy)sulfonyl Isocyanates: Synthesis of N-Acylsulfamates, Disulfamates, and N,N′-Disulfonylureas

Abstract Reaction of carboxylic acids with aroxy(alcoxy)sulfonylisocyanates allowed the preparation of the corresponding aroxy(alcoxy) N-acylsulfamates. With succinic diacid, the same reaction yielded the corresponding N, N′-diacylsulfamates, whereas the N, N′-disulfonylureas were obtained by reaction of maleic or fumaric diacids.

Synthesis of New Perfluoroalkylated 1,3,4-Oxadiazoles and 1,2,4-Triazoles Starting from 2-(Perfluoroalkyl)ethane Thiols

Abstract 5-{[2-(Perfluoroalkyl)ethylthio]methyl}-1,3,4-oxadiazole-2-thiones 4a, b and 4-amino-5-{[2-(perfluoroalkyl)ethylthio]methyl}-4H-1,2,4-triazole-3-thiones 5a, b have been prepared from 2-(perfluoroalkyl)ethane thiols 1a, b through a multistep reaction sequence. Compounds 4a, b were further reacted with aryloxysulfonylisocyanates to give the corresponding 5-{[2-(perfluoroalkyl)ethylthio]methyl}-N-(aryloxysulfonyl)-2-thioxo-1,3,4-oxadiazole-3(2H)-carboxamide 6a–d. The new products were obtained in good to moderate yields, and their structures were established on the basis of their infrared, NMR, and mass spectral data.

Formation of N‐Sulfonylcarbamates from Epichlorohydrin: Synthesis of Polyfunctional Oxazolidin‐2‐ones

Abstract The addition of 3‐methylbut‐2‐enoic acid‐3‐bromo‐2‐hydroxypropyl ester 2 and 1‐bromo‐3‐phenylsulfanyl propan‐2‐ol 3, obtained from epichlorohydrin, to aroxy and alkoxysulfonyl isocyanates 1 in anhydrous ether at ambient temperature affords the corresponding N‐sulfonyl bromocarbamates 4. These are treated with triethylamine in refluxing acetone to give exclusively the corresponding polyfunctional oxazolidin‐2‐ones 5 with good yields.

Addition of various unsaturated alcohols to sulfonylisocyanate derivatives: Synthesis of new unsaturated N-sulfonyl carbamates

GRAPHICAL ABSTRACT Abstract The synthesis of new unsaturated N-sulfonylcarbamates by the addition of unsaturated alcohols to aroxy(alkoxy)sulfonylisocyanates is reported. The reaction is carried out at room temperature in the presence or absence of solvent, depending on the nature of the starting alcohol. The products were obtained in good yields and characterized with IR, 1H, and 13C NMR and HRMS analyses.

Synthese des Aroxy(alcoxy)sulfonyl-5-F-hexyl Oxazolidin-2-ones

The addition of 1-F-hexyl-2-bromoethanol and 2-F-hexyl-2-bromoethanol to aroxy-or alkoxysulfonyl isocyanates in anhydrous ether allowed the preparation of the corresponding brominated F-alkyl carbamates. In the case of 1-F-hexyl-2-bromoethanol, the easy cyclization of carbamates to F-alkyl oxazolidin-2-ones was achieved by the action of triethylamine in refluxing acetone.

Synthesis of Nonionic Aroxylsulfonyl Carbamates

Novel aroxylsulfonyl carbamates containing polar head or core type were synthesized from the action of aroxysulfonylisocyanate on oligooxyethylmonomethylated ethers or glycols without solvent. At room temperature the reaction occurs rapidly with satisfactory yields. The synthetic pathway of isocyanate derivatives is achieved in a one-pot reaction in order to use low price commercially available compounds such as phenolic derivatives and chlorosulfonylisocyanate as starting materials. This new class of nonionic compounds contains one aromatic part and one polar part. All these compounds are monodisperse, that is, they include a perfectly defined number of oxyethylene units. The synthesis and characterization of these new series of carbamates are described.