A Simple Method for Generation of Thiocarbonyl Ylides and Their Regioselective 1,3-Cycloadditions

Abstract

Thioketone S-methylides were generated from thioketones and (trimethylsilyl)methyl triflate, and underwent 1,3-cycloaddition with thioketones to give 1,3-dithiolanes.

ChemInform Abstract: 1,3‐Dipolar Cycloadditions. Part 117. Reactions of Thiobenzophenone S‐Methylide with Thiocarbonyl Compounds.

“…[11] Apart from the conversion of 7a to tetraphenylethylene, the 13 C NMR parameters reveal the C 2v symmetry of 7a and other "Schönberg products", which bear identical substituents in 4-and 5-positions. Thus, the reactants combine in the sterically hard way by bond formation between the centers bearing the voluminous substituents.…”

Conformational behavior of 3,3-dimethyl-3-silathiane 1-oxide and its diastereomeric 2-methyl derivatives

“…The usefulness of α-silyl sulfoxides for the preparation of various types of carbonyl compounds [1], vinyl sulfoxides [1] and heterocycles [1,3,4] has been demonstrated. β-Silyl sulfoxides can serve as a vinyl anion equivalent for the regiospecific synthesis of olefins and as suitable precursors for obtaining alkane-, arene-and 1-alkenesulfenyl chlorides [2].…”

Chemoselectivity of the [2 + 3]‐Cycloaddition of Thiocarbonyl Ylides with 5‐Benzylidene‐3‐phenylrhodanine.

“…Aromatic thioketone S-methylides 1 react with aromatic as well as cycloaliphatic thioketones (e.g. 2 and 3) to give the sterically crowded 1,3-dithiolanes of type 4 and 5, respectively, in a regioselective manner [14,15,19]. On the other hand, the reactions of cycloaliphatic thioketone S-methylides, such as 6 with 2, lead to mixtures of 1,3-dithiolanes, e.g.…”

“…ESI-MS (MeOH + NaI): 532 (100, [M +Na] + ). (Z)-5-Benzylidene-2-diphenylmethylene-3-phenyl-1,3-thiazolidin-4-one(19). A slightly acidic solution of 18 in CDCl 3 turned yellow and a solid precipitated.…”