A facile method for the synthesis of substituted 2-ylidene-1,3-oxathioles from acetophenones

Tetrahedron Letters

Volumn 48, Issue 47, 2007, Pages 8376-8378

  Samuel, R ^a   Asokan, C V ^a   Suma, S ^a   Chandran, P ^a   Retnamma, S ^a   Anabha, E R ^a  

^a MAHATMA GANDHI UNIVERSITY   (India)

Author keywords

Oxoketene dithioacetals; 1,3 Oxathioles; Active methylene ketones; Dithiocarboxylates

Indexed keywords

2 YLIDENE 1,3 OXATHIOLE DERIVATIVE; ACETOPHENONE DERIVATIVE; BETA OXODITHIOCARBOXYLATE DERIVATIVE; BROMOACETONE; CARBOXYLIC ACID DERIVATIVE; KETONE DERIVATIVE; METHYLENE KETONE; PHENACYL BROMIDE; TRITHIOCARBOXYLATE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; INFRARED SPECTROMETRY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SUBSTITUTION REACTION; THIN LAYER CHROMATOGRAPHY;

EID: 35348996543     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.09.076     Document Type: Article

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33. Synthesis of β-Oxodithiocarboxylates; general procedure: acetophenone 1 (20 mmol) was added to a suspension of NaH (50% suspension in mineral oil, 1.92 g, 40 mmol) in DMF/hexane solvent mixture (50 mL, 1:10; hexane bp 40-65 °C). Trithiocarbonate (20 mmol) was added to the solution and stirred well for 1 h. The reaction formed an interface between the two layers present in the reaction mixture. The reaction was exothermic and the reaction mixture was cooled in a water bath at room temperature. After 1 h, the reaction mixture was acidified with 1 N HCl (20 mL). The precipitated dithiocarboxylates 2 were filtered, dissolved in dichloromethane, dried over anhydrous sodium sulfate and the solvent was evaporated to give the corresponding β-oxodithiocarboxylates in good yields.
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