ChemInform Abstract: Hydrolysis of N‐(2,2,2‐Trichloroethyl)arenesulfonamides.

Abstract

Hydrolysis of N-(2,2,2-Trichloroethyl)arenesulfonamides.-The direction of hydrolysis of title compounds is found to depend on the substituent in α-position with respect to the nitrogen atom. Sulfonamides (I) bearing a p-donor heteroatom in the aforesaid α-position yield N-unsubstituted sulfonamides (II), whereas α-aryl-substituted sulfonamides (III) afford chemoselectively the corresponding carboxylic acids (IV). -(ROZENTSVEIG, I. B.; LEVKOVSKAYA, G. G.; MIRSKOVA, A. N.; KASHIK, T. V.; Russ.

Reduction of N-(polychloroethylidene)- and N-(1-hydroxypolychloroethyl) arenesulfonamides with adamantane in the presence of superacids

“…The action of alkaline reagents on hemiaminals like V and VI could give rise to transformations involving elimination of sulfonamide molecule, as we showed previously [16]. The reduction procedure with the use of adamantane is free from the above disadvantages, so that it can be successfully applied to halogencontaining Schiff bases and their functionalized derivatives, and synthetic potential of these important reagents can be considerably extended.…”

Reaction of 4-chloro-N-(2,2,2-trichloroethylidene)benzenesulfonamide with allyl- and propargylzinc bromides

“…IR spectrum (KBr), ν, cm -1 : 3267 (NH), 1644 (C=C), 1340, 1165 (SO 2 ). 1 The IR spectra were recorded on a Bruker IFS-25 spectrometer. The 1 H and 13 C NMR spectra were measured from solutions in DMSO-d 6 on a Bruker DPX-400 spectrometer at 400.61 and 100.13 MHz, respectively, using tetramethylsilane as internal reference.…”

10.1007/s11178-008-2006-7

“…Polyfunctionsl halogen-containing ethylamides of sulfonic acids are initial compounds for preparation of amino acids [8], amidine derivatives of amino acids [9], and heterocyclic compounds [10,11]. Polyfunctionsl halogen-containing ethylamides of sulfonic acids are initial compounds for preparation of amino acids [8], amidine derivatives of amino acids [9], and heterocyclic compounds [10,11].…”