Abstract
Symmetric organic bis-sulfides were prepared via reductive thiolation of dicarbonyl compounds with thiols or of carbonyl compounds with dithiols in the presence of triethylsilane and boron trifluoride monohydrate.
Highlights
Organic bis-sulfides are generally synthesized by the nucleophilic substitution of alkyl halides with thiolates.[2]
1-n-butylthio-2-(1,1diaryalkylthio)ethanes and –propanes can be obtained by treating corresponding 2,2-diaryl-1,3-dithiolanes and –1,3-dithianes with nbutyl lithium followed by addition of alkyl halides.3a Vicinal bissulfides were prepared by either BF3 catalyzed addition of disulfides to alkenes or radical addition of two molar equivalents of thiol to acetylenes.3b,c
The reaction, led to complex mixtures of products. This is in contrast to what was earlier observed in the monothiolation of carbonyl compounds with 2-methyl-2-propanethiol
Summary
Organic bis-sulfides are generally synthesized by the nucleophilic substitution of alkyl halides with thiolates.[2].
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