Synthesis of novel trithiocarbonate-S-oxides

• The oxidation of the trithiocarbonates 3 with m-chloroperoxybenzoic acid (m-CPBA) in chloroform at room temperature provides an efficient stereoselective synthesis of the (E) sulfine 4(a) and (Z) sulfine 4(b). The expected (E) and (Z) configurations of 4(a,b) were confirmed by x-ray structure determination. The Sulfines 4 were further structurally elucidated by their cycloaddition reactions with 2,3-dimethyl-1,3-butadiene in chloroform at room temperature to give the corresponding dihydrothiopyran S-oxides 5(a,b) in a quantitative yield.

Nyckelord

chlorodithioformates

dihydrothiopyran-S-oxide

oxidation

sulfines

trithiocarbonate

aliphatic sulfines

convergent synthesis

thiophilic addition

silyl thioketones

chemistry

oxidation

organolithiums

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