E. Bollens

Reactivite des (F-alkyl-2 ethylthio)methanols : synthese de nouveaux agents tensio-actifs cationiques

Abstract Reaction of (2-F-alkyl ethylthio) methanols with phosphorus tribomide or trichloride leads to α-halogenated sulfides. These compounds, frequently described in hydrocarbon chemistry, are unknown when substituted by a F-alkyl group. New cationic surfactants are obtained by reaction of these halides with tertiary amines and phosphines. They are characterised by the presence of only one methylene group between the sulfur and the nitrogen or phosphorus atoms. Some special structures and the properties which might be expected are discussed.

Réactivité des isothiocyanates de 2-F-alkyléthyle et de leurs isomèrs avec les ylures de phosphore stabilisés

Abstract This work reports on the reactivity of 2- F -alkylethyl thiocyanates and isothiocyanates towards stabilized phosphonium ylides. The results led to a new method being devised which allowed the introduction of a perfluoroalkyl chain into the structure of a stabilized phosphonium ylide. The method has been extended with thiocyanates to allow the introduction of an alkyl or alkylaryl chain into such a structure.

Réactivité des iminophosphoranes F-alkylés : Synthèse de F-alkyl β-dicétones

Abstract In contrast to aliphatic hydrocarbon-type nitriles, F-nitriles react with activated phosphorus ylides, to give the corresponding iminophosphoranes. When the F-alkyl group is a long chain (other than CF3) they are easily hydrolysed in acidic media, and lead to the corresponding β-diketones in quantitative yields. More, this method shows an advantage in avoiding the intermediate formation of metallic chelates, from which it is necessary to isolate β-diketones obtained by the usual ways.

Synthèse d'iminocétènes F-alkylés, voie d'accès aux F-alkyl-β-amido esters substitués en position pseudo-malonique

Abstract New F -alkyl iminoketenes [R F C 2 H 4 NC ; R F C 4 F 9 , C 6 F 13 ; RCH 3 , C 2 H 5 ; R′CH 3 , C 2 H 5 , n−C 3 H 7 ] prepared from 2- F -alkyl ethyl isothiocyanates give, on hydration, F -alkyl-β-amido esters which are potential precursors of F -alkylated heterocycles.

Synthèse et réactivité du bromo-2 (F-éthyl-2 éthyl thio)-1,3 propane

Abstract In this paper we have reported the synthesis and reactivity of 2-bromo 1,3-di (2-F-ethyl ethyl thio) propane. New compounds, especially those resulting from removal of bromine in alcoholic or basic media, are unambigously identified by mass spectrometry. Mechanisms requiring a thiiranium are discussed. For the first time such a F-alkyl substituted intermediate is involved.