Stereoselective synthesis of E-vinyl sulfides from alkynes in water under neutral conditions using β-cyclodextrin

Synlett

Volumn , Issue 20, 2006, Pages 3495-3497

  Sridhar, R ^a   Surendra, K ^a   Srilakshmi Krishnaveni, N ^a   Srinivas, B ^a   Rama Rao, K ^a  

^a INDIAN INSTITUTE OF CHEMICAL TECHNOLOGY   (India)

Author keywords

cyclodextrin; Aromatic alkynes; E vinyl sulfides; Thiophenols; Water

Indexed keywords

ALKYNE DERIVATIVE; AROMATIC CARBOXYLIC ACID; BETA CYCLODEXTRIN; METAL; SULFIDE; THIOPHENOL DERIVATIVE; VINYL DERIVATIVE; WATER;

ADDITION REACTION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; STEREOCHEMISTRY; SYNTHESIS;

EID: 33846533074     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-956458     Document Type: Article

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48. General Procedure: β-Cyclodextrin (1 mmol) was dissolved in H2O (1 mL) by warming to 60 °C until a clear solution was formed. Then alkyne (1 mmol) dissolved in acetone (1 mL) was added dropwise and the mixture was allowed to cool to r.t. Thiol (1 mmol) was then added and the mixture was stirred at r.t. until the reaction was complete (Table 1). The organic material was extracted with EtOAc, the extract was dried and concentrated under reduced pressure and the resulting product, although seen as single compound by TLC, was further purified by passing through a column of silica gel. The cyclodextrin was recovered by filtration and reused.
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