An economical and convenient preparation of 2-(phenylthio)cyclobutanone, a synthetic equivalent of cyclobutanone

Carbon–Carbon Bond-Forming Reactions of α-Thioaryl Carbonyl Compounds for the Synthesis of Complex Heterocyclic Molecules

“…Following the examples of Gleason, whose protocol is specifically for enolate generation, we treated lactam 16 with LiDBB and observed decomposition of the starting material after attempted trapping with electrophiles or protonation (Table ). Close inspection of the proline-derived substrates used by Gleason revealed that most were devoid of multiple-bonded functionality that might be more easily reduced than the desired C–S bond. , We next attempted SmI 2 and observed no reaction . The authors of ref note that related reactions of γ-lactams were unsuccessful, suggesting that the additional inductive stabilization in a succinimide enolate intermediate facilitates the reduction by SmI 2 in that case.…”

“…C–S bond breakage under reducing conditions to produce an anion is relatively straightforward, depending on the stability of the anion that is formed. In the case of enolate formation, recent examples of reducing agents for this process include lithium-di- tert -butyl biphenyl (LiDBB) and SmI 2 . We also set out to explore the possibility of using the sulfide group of 4CR products as a radical precursor.…”

Enantioselective Synthesis of (−)-Maoecrystal V by Enantiodetermining C–H Functionalization

“…If successful, the nitro or phenylthio group could be removed by reduction under radical conditions. 39 …”

Lithium Carbenoids

“…There is also evidence for a carbenoid character in lithiated acetals 352 , lithiated thioacetals 353 and tris(phenylthio)methyllithium 354 . Reactivity typical of carbenoids is also displayed by α-lithiated vinyl ethers.…”