Nucleophilic Substitution and Redox Reactions with alpha-Chloro beta-Oxo Sulfenyl Chlorides

Farag A.G. El-Essawy, Salah M. Yassin, Ibrahim A. El-Sakka, Ahmed F. Khattab, Inger Søtofte, Jørgen Øgaard Madsen, Alexander Erich Eugen Senning

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Alpha-Chloro sulfenyl chlorides such as 1 and 4 could not be reduced to the corresponding disulfides. Under reducing conditions they are instead dechlorinated to the corresponding thiocarbonyl compounds. Starting from the chroman-4-one derivatives 1 a number of 1,3,4-oxadithiins 3 have been prepared. Sulfenyl chlorides 1 and 4 have been derivatized with p-toluenesulfinate, methoxide, and cyanide ions as well as with primary and secondary amines, with thiophenol and with thiobenzoic acid. The molecular structure of thiocyanate 8a has been determined by X-ray crystallography.
Original languageEnglish
JournalSulfur Letters
Pages (from-to)19-32
Publication statusPublished - 1998

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