146550-19-8

Basic information

• Product Name: (Z)-1-methylthio-1-(2-propenylthio)-3-phenyl-1-butene
• CAS NO: 146550-19-8
• Molecular Weight: 250.429
• Mol File: 146550-19-8.mol

Chemical Properties

• CAS DataBase Reference: (Z)-1-methylthio-1-(2-propenylthio)-3-phenyl-1-butene(CAS DataBase Reference)
• NIST Chemistry Reference: (Z)-1-methylthio-1-(2-propenylthio)-3-phenyl-1-butene(146550-19-8)
• EPA Substance Registry System: (Z)-1-methylthio-1-(2-propenylthio)-3-phenyl-1-butene(146550-19-8)

Safety Data

• Hazardous Substances Data: 146550-19-8(Hazardous Substances Data)

Upstream product

• 146550-10-9 methyl 3-phenylbutanedithioate 
• 106-95-6 allyl bromide 

Downstream Products

• 146550-22-3 methyl 2-(1-phenylethyl)-4-pentenedithioate 

Relevant articles and documents

Acyclic Stereocontrol through the Thio-Claisen Rearrangement of Precursors bearing a Chiral Centre adjacent to Carbon 1

The Claisen rearrangement of precursors bearing a stereogenic centre adjacent to carbon 1 of the pericyclic nucleus has been investigated in the sulfur series.Dithioesters having a methyl and various alkyl or alkenyls groups on the β-carbon were deprotonated by LDA.The resulting enethiolates were allylated on sulfur to give S-allyl ketenedithioacetals.The thio-Claisen transposition of the latter compounds was achieved either at room temperature or at 101 deg C to afford good yield of allylated dithioesters.Diastereomeric selectivities up to 95:5 have been observed.These results have been explained by a steric effect and correlated to allylic strain values.

Recent Synthetic Developments in Thiocarbonyl Chemistry

Direct oxidation of enethiolizable thioketones and dithioesters with a peroxycarboxylic acid affords the corresponding sulfines quantitatively.This observation stands in contrast with literature expectations, stating that this reaction would lead to divinyl disulfides.The oxidation shows a high stereoselectivity: delivery of the oxygen proceeds from the side opposite to the alkylthio group of dithioesters and from the side opposite to the more hindered substituent in the case of thioketones.The thermal stability of these sulfines was studied and a novel rearrangementwas observed.The second part of this report deals with the thio-Claisen rearrangement of precursors bearing a chiral centre adjacent to the pericyclic nucleus and its use for stereocontrol in the acyclic series.This thermally facile transposition leads to allylated dithioesters with good to excellent yields.A high diastereomeric selectivity was obtained in a number of cases involving either a steric effect with alkyl groups on the chiral centre or a noteworthy electronic effect when this centre bears a heteroatomic group.It was also carried out in the homochiral series.A favoured conformation and approach model is proposed to explain the formation of syn isomers.