Highly Stereoselective One-Pot Procedure To Prepare Bis- and Tris-chalcogenide Alkenes via Addition of Disulfides and Diselenides to Terminal Alkynes

Abstract

We present here the reaction of diorganoyl dichalcogenides with terminal alkynes under catalyst-free conditions, by a one-pot procedure, to prepare bis- and tris-chalcogenide alkenes selectively, avoiding the previous preparation of chalcogen alkynes. The reaction proceeded cleanly under mild reaction conditions, and the addition of dichalcogenides to alkynes occurred stereoselectively to give exclusively the corresponding Z isomers. We observed that the selectivity control was governed by the effective participation of the hydroxyl group from propargyl alcohols. In addition, the bis-chalcogenide alkenes were exclusively obtained with propargyl alcohol having the acidic hydroxyl group proton. Conversely, the alkynes with no potentially acidic hydroxyl group proton, at propargyl positions, gave exclusively the tris-chalcogenide alkenes.

Role of nitric oxide/cyclic GMP/K+ channel pathways in the antinociceptive effect caused by 2,3-bis(mesitylseleno)propenol

“…1), was prepared and characterized according to Moro et al (2005). Analysis of the 1 H NMR and 13 C NMR spectra showed analytical and spectroscopic data in full agreement with its assigned structure.…”

Depression-like behavior and mechanical allodynia are reduced by bis selenide treatment in mice with chronic constriction injury: a comparison with fluoxetine, amitriptyline, and bupropion

“…Bis selenide [(Z)-2,3-bis(4-chlorophenylselanyl)prop-2-en-1-ol] was prepared and characterized in our laboratory by the method previously described (Moro et al 2005). Analysis of the 1 H NMR and 13 C NMR spectra showed analytical and spectroscopic data in full agreement with its assigned structure.…”

Stereoselective Synthesis of (Z)-1,2-Diarylthio-1-alkene via the Reaction of Diaryl Disulfides with Terminal Alkynes Catalyzed by Cesium Hydroxide

“…Among the common vinyl sulfides, 1,2-dithio-1-alkenes are of much importance because of their use as bidentante ligands in coordination chemistry, precursors of new optical materials for microelectronics, [1] and important intermediates for organic synthesis. Traditionally there are two kinds of paths for the preparation of 1,2-dithio-1-alkenes: one involves the addition of disulfides to terminal alkynes [3][4][5][6][7][8][9][10][11] and the other is the addition of thiol to alkynyl sulfides. [12][13][14][15][16][17] In most cases, both methods need transition-metal catalysis.…”