Organic Sulfur Compounds. XIII.¹ Free-Radical Addition of Thiols to Phenylacetylene²

A simple and general preparation of vinylic sulfides, selenides and tellurides

“…The reaction with the internal halo alkenes 4f-g followed a different pathway, and the corresponding Z-vinylic sulfides 5c and 8 were isolated. In this case, in view of the lower nucleophilic character of the thiolate anion, the formed product suggests that a prior elimination reaction was occurring, generating the terminal alkyne followed by trans-selective addition of the thiol or thiolate giving the corresponding Z product, as expected from previous results [31,32]. We next turned our attention to the selenium derivatives, reacting with the same vinylic halides.…”

Polyaddition of Dithiol Compounds to Diethynyl Compounds: Kinetics of the Model Addition Reaction of Thiophenol to Ethynylbenzene

“…In the addition reactions of thiol compounds to ethynyl compounds, the stereochemistry has been studied in detail, 16 but kinetic investigation has been done only scarcely. The addition reaction of thiophenol to ethynylbenzene is considered to progress by a chain mechanism similar to the addition reaction ofthiophenol to styrene.…”

Thiol‐Ene Radical Addition of L‐Cysteine Derivatives to Low Molecular Weight Polybutadiene

“…[16][17][18][19][20][21][22][23][24][25][26][27][28] Another remarkable mechanism aspect was a noticeable anti-Markovnikov behaviour of the addition reaction. [6,7,14,15,29,30] During the 1980s, Priola et al [27,28] obtained functionalised PBLs with 2-mercaptoethanol, TGA, 3-mercaptopropanoic acid or (mercaptopropyl)trimethoxy silane (MPTS) by using photoinitiators under UV lighting. Gorski and coworkers [19,24,25] used 8-mercaptooctan-1-ol or MPTS [24,25] with the same polymeric substrates to obtain a PB that, under particular conditions, could undergo a sol-gel process by creating a cross-linked resin.…”