42075-43-4Relevant academic research and scientific papers
Reactions of In-Situ Generated Acyllithium Reagents with Carbon Disulfide and Carbonyl Sulfide.
Seyferth, Dietmar,Hui, Richard C.
, p. 2623 - 2626 (1984)
In-situ generated (at -110 deg C to -135 deg C) acyllithium reagents, RC(O)Li (R=t-Bu, n-Bu), react with CS2 to give Li with loss of CS.On the other hand, COS reacts to give Li.
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.
METALLATION ET ALKYLATION DES THIOIMIDOESTERS: APPLICATION EN SYNTHESE
Masson, S.,Mothes, V.,Thuillier, A.
, p. 1573 - 1580 (2007/10/02)
Alkylation of delocalized anions resulting from metallation of N-phenyl thioimidoesters (precursors of dithioesters and thiolesters) takes place on nitrogen with "saturated" thioimidoesters (alkane thiomidates).On the contrary, unsaturated thiomidoesters (α or β-ethylenic, α-arylated) are regioselectively alkylated on the α carbon atom by alkyl or allylic halides.The possibilities for synthesis offered by successive uses of the reactivities of thioimidoester and dithioester functions (allowing in particular two electrophilic additions on two vicinal carbons) are illustrated by syntheses of terpenic compounds lavandual (and lavandulol) and ar-curcumene.
