Electrodic cleavage of the N–S bond in N-tosylcarboxamides. A new entry to N-unsubstituted lactams

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Abstract
The electrochemical reduction of different types of N-tosylcarboxamides under various experimental conditions has been investigated. It has been found that in all instances the N–S bond is selectively cleaved with respect to the N–C bond, thus providing a new method for the deblocking of the tosyl group from such substrates. As a consequence, a two-step electrochemical synthesis for N-unsubstituted lactams is now available, which has been simplified to a one-pot procedure in the case of synthetically important azetidin-2-ones.