Thiophilic addition of organolithiums to trithiocarbonate oxides (sulfines): Synthesis of β-oxoketene dithioacetals, 1, 4-dicarbonyl compounds, and allyl sulfoxides

…, P Metzner, A Capperucci, A Degl'Innocenti

Index: Leriverend, Catherine; Metzner, Patrick; Capperucci, Antonella; Degl'Innocenti, Alessandro Tetrahedron, 1997 , vol. 53, # 4 p. 1323 - 1342

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Citation Number: 20

Abstract

Reaction of trithiocarbonates with meta-chloroperoxybenzoic acid in CH2Cl2 at 0° C affords the corresponding S-oxides. These sulfines are relatively stable compounds which can be purified by chromatography. They react readily with organolithiums in THF at− 78° C in a thiophilic manner to give carbanions which are stabilized by three sulfur groups. Hydrolysis affords trithioorthoester oxides. The thermal behaviour of these hindered products has ...