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Synthesis and cathodic cleavage of a set of substituted benzenesulfonamides including the corresponding tert-butyl sulfonylcarbamates: pKa of sulfonamides

DOI: 10.1039/P19950002025

Source and publish data:

Journal of the Chemical Society. Perkin transactions I p. 2025 - 2032 (1995)

Update date:2022-08-03

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Authors:

Nyasse, BarthelemyNyasse, Barthelemy

Grehn, LeifGrehn, Leif

Ragnarsson, UlfRagnarsson, Ulf

Maia, Hernani L. S.Maia, Hernani L. S.

Monteiro, Luis S.Monteiro, Luis S.

et al.et al.

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Article abstract of DOI:10.1039/P19950002025

From a series of substituted benzenesulfonic acids, most of which have previously been employed for the protection of amino functions and including a few such known to facilitate cleavage by acid, benzylamides 1a-k have been derived and studied.Initially their electrochemical cleavage potentials were determined by cyclic voltammetry in order to further explore selective deprotection within this substance group.In parallel, the corresponding tert-butyl sulfonylcarbamates 2a-k have also been prepared and studied.Among the sulfonamides investigated S-N bond cleavage was found to take place over a wide range of potentials from -1.67 to -2.64 V (excluding the nitro derivative), the most acid-labile groups requiring more negative potentials, whereas this cleavage was facilitated by 0.19-0.39 V for the sulfonylcarbamates.Small scale electolyses of 2 at controlled potential with determination of the cleavage products formed were subsequently performed.For the N-benzylbenzenesulfonamides, 1, the pKas in DMSO and in some cases also in water have been determined and found to be in the range 14.0-16.4 and 10.07-11.53, respectively.

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