Vinyl Sulfides from Thioacetals with Copper(I) Trifluoromethanesulfonate: ( Z )‐2‐Methoxy‐1‐Phenylthio‐1,3‐Butadiene

Abstract

Vinyl sulfides from thioacetals with copper(I) trifluoromethanesulfonate: ( Z )‐2‐methoxy‐1‐phenylthio‐1,3‐butadiene intermediate: Bis(phenylthio)methane intermediate: 4,4‐ Bis(phenylthio) ‐3‐ methoxy ‐1‐ butene product: (Z)‐2‐ Methoxy ‐1‐ phenylthio ‐1,3‐ butadiene reactant: 3.27 g. [0.00650 mole, 0.0126 g.‐atom of copper(I)] of bis[copper(I) trifluoromethanesulfonate] benzene complex reactant: Thiophenol was purchased from Aldrich Chemical Company, Inc. reactant: Acrolein was purchased by the submitters from Cationics, Division of Columbia Organic Chemicals Company, Inc. (Columbia, South Carolina)

Activation of Si–Si Bonds for Copper(I)‐Catalyzed Conjugate Silylation

“…After screening the copper sources with the use of cataCXiumA as the ligand in DMF at 100 °C (Table 1, Entries 1–3), (CuOTf) 2 ·C 6 H 6 [16] appeared as the most efficient salt, yielding 2a in 38% yield, whereas CuI gave a lower yield of 33%. Surprisingly, no reaction occurred with CuCl.…”

Total Synthesis of (−)-Ardeemin

“…Under N 2, to a solution of 7 (50 g, 0.22 mol) and a freshly made CuOTf−toluene complex (25 g, 0.043 mol) in dry toluene (200 mL) was slowly added a solution of diazo 8 (100 g, 0.88 mol) in dry CH 2 Cl 2 (1000 mL) at 25 °C. The reaction mixture was stirred at room temperature for 6 h and then was concentrated.…”

Bis(benzylsulfanyl)methane

“…For the synthesis of the title ligand, see: Cohen et al (1980). For related structures, see: Li et al (2005); Tanaka & Ajiki (2005).…”

“…The title compound was synthesised according to the published procedure (Cohen et al, 1980) and recrystallized from petroleum ether.…”