Abstract
A comparative study has been performed on ethyl-methyl- and diethyl-mercaptoacetic acid (1 and2), and thianeaceticacid betain (3) with respect to their reactivity towards haloacetic acid anhydrides and 4-nitrobenzene-diazonium tetrafluoroborate. The results show that in analogy to related N-betaines the alkyl substituents at the cationic reaction center display a strong influence on reactivity. The most stable S-ylides are obtained from the cyclic S-betain3 in high yield. The1H-NMR spectra reveal that the protons of the methylene groups in compounds1–3 are fully exchanged for deuterium (in D2O) in contrast to the behavior of the corresponding N-betaines.
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