Convenient Horner-Wittig-based synthetic approaches to the preparation of (diphenylphosphinoyl)methyl vinyl sulfides as well as symmetrically and unsymmetrically substituted divinyl sulfides, are described. The syntheses involve the use of the easily available bis[(diphenylphosphinoyl)methyl] sulfide as a common starting material and sodium hydride as base, in tetrahydrofuran. sulfur - Wittig reaction
Triphenylethenethiol. Structure, Equilibria with the Thioketone, Solvation, and Association with DMSO
作者:Tzvia Selzer、Zvi Rappoport
DOI:10.1021/jo9604651
日期:1996.1.1
The simple thioenols, triphenylethenethiol (12) and 2,2-diphenyl-1-anisylethenethiol (13) were prepared. Both are the only observed constituent of the thioenol reversible arrow thioketone equilibria and comparison and estimation suggested that the thiocarbonyl reversible arrow thioenol equilibrium constant K-enol for 12 and other simple thioenols is greater than or equal to 10(6) higher than for the corresponding carbonyl reversible arrow enol equilibria. The X-ray diffraction of 12, which is the first measured for a simple thioenol, shows a propeller arrangment of the three rings. The delta(SH) in the H-1 NMR spectrum increases with the increase in the hydrogen bonding accepting parameter beta of the solvent. The association constant K-assoc of 12 with DMSO is 0.087, much lower than values of triarylethenols with DMSO. Reaction of diphenylacetaldehyde with Lawesson's reagent did not give the thioenol, but gave bis(2,2-diphenylvinyl) sulfide (16) and a substance (17) having a trithiaphosphorinane system.
AMOSOVA S. V.; TARASOVA O. A.; TROFIMOV B. A.; KALABIN G. A.; BZHEZOVSKIJ+, ZH. ORGAN. XIMII <ZORK-AE>, 1975, 11, HO 10, 2026-2034
作者:AMOSOVA S. V.、 TARASOVA O. A.、 TROFIMOV B. A.、 KALABIN G. A.、 BZHEZOVSKIJ+
DOI:——
日期:——
<i>N</i>-Vinylthio Phthalimides (<i>N</i>-VTPs): Modular Reagents for Vinylthio AIEgen Transfer