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Synthesis 1990; 1990(9): 819-822
DOI: 10.1055/s-1990-27025
DOI: 10.1055/s-1990-27025
paper
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Oxokohlenstoffe und verwandte Verbindungen; 16. Mitteilung1. Synthese von 3-Alkylthio- und 3-Arylthio-3-cyclobuten-1,2-dionen (Thiosemiquadratsäure-S-estern)
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Publication History
Publication Date:
17 September 2002 (online)
Oxocarbons and Related Compounds; Part 16.1 Synthesis of 3-Alkylthio- and 3-Arylthio-3-cyclobutene-1,2-diones (S-Alkyl and S-Aryl Thiosemisquarates) The reaction of semisquaric chloride (1) with thiols 2 (X = H) has been investigated. In the presence of triethylamine (Method A) only moderate yields of S-alkyl thiosemisquarates 3a-d were obtained. Moderate to good yields of S-alkyl and S-aryl thiosemisquarates 3a-f were obtained in the presence of aluminum chloride (Method B) and by the reaction of 1 with trimethylsilyl sulfides 2 (X=SiMe3) in the presence of aluminum chloride (Method C).