83994-44-9Relevant academic research and scientific papers
Synthetic Application of Lithiated Tris(methylthio)methane: Preparation of Aliphatic Methyl Thiolcarboxylates from the Corresponding Halides. Convenient Synthesis of Tris(methylthio)methane
Barbero, Margherita,Cadamuro, Silvano,Degani, Iacopo,Dughera, Stefano,Fochi, Rita
, p. 2075 - 2080 (2007/10/02)
A thorough study directed towards the synthesis of methyl thiolcarboxylates was made on the basis of the following steps: (i) conversion of alkyl halides into the corresponding trimethyl trithioorthocarboxylates by using tris(methylthio)methyllithium in THF at -78 degC; (ii) selective hydrolysis of the intermediates to methyl thiolcarboxylates by using 35percent aq.HBF4 in DMSO or, in some cases, in THF.The overall yields of the two stages are, usually, between 70 and 88percent.By this procedure it is also possible to incorporate 18O in the carbonyl group of thiol esters (ca. 98percent isotopic purity).Furthermore, a new, convenient method for the preparation of tris(methylthio)methane as the precursor of tris(methylthio)methyllithium was developed.
Synthesis of Acenaphthene-1-carboxylic Acid Using Lithiated Tris(methylthio)methane to Carboxylate 1-Bromoacenaphthene
Halfpenny, Paul R.,Horwell, David C.,Rees, David C.
, p. 517 - 519 (2007/10/02)
A new synthesis of acenaphthene-1-carboxylic acid (4) in 3 steps and 78 percent overall yield from 1-bromoacenaphthene (1) is described.In the key step, lithiated tris(methylthio)methane is reacted with 1-bromoacenaphthene to give 1-acenaphthene (2).Methanolysis of 2 gives racemic methyl acenaphthene-1-carboxylate 3, which is resolved by chiral chromatography.The usefulness of tris(methylthio)methyllithium as a carboxyl carbanion equivalent is illustrated by the conversion of three other bromides to the corresponding methoxycarbonyl derivatives.
NEW SYNTHESIS OF KETENE THIOACETALS, VINYLSULFIDES AND THEIR SELENO ANALOGUES
Denis, J. N.,Krief, A.
, p. 3407 - 3410 (2007/10/02)
Title compounds have been prepared on reaction of thioacetals, orthothioesters and their seleno analogues with diphosphorus tetraiodide (P2I4) or phosphorus triiodide (PI3).
