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In organosulfur chemistry, the thiol-ene reaction (also alkene hydrothiolation) is an organic reaction between a thiol (R−SH) and an alkene (R 2 C=CR 2) to form a thioether (R−S−R'). This reaction was first reported in 1905, [1] but it gained prominence in the late 1990s and early 2000s for its feasibility and wide range of applications.
The OSTE resins are cured via a rapid thiol-ene "Click" reaction between thiols and allyls. The thiols and allyls react in a perfectly alternating fashion and has a very high conversion rate (up to 99%), [5] the initial off-stoichiometry of the monomers will exactly define the number off unreacted groups left after the polymerization.
However, several reactions have been identified that fit the concept better than others: [clarification needed] [3+2] cycloadditions, such as the Huisgen 1,3-dipolar cycloaddition, in particular the Cu(I)-catalyzed stepwise variant, [6] are often referred to simply as Click reactions; Thiol-ene reaction [7] [8]
Thiyl radicals are intermediates in the thiol-ene reaction, which is the basis of some polymeric coatings and adhesives. They are generated by hydrogen-atom abstraction from thiols using initiators such as AIBN: [2] RN=NR → 2 R • + N 2 R • + R′SH → R′S • + RH. Thiyl radicals are also invoked as intermediates in some biochemical ...
Pentaerythritol tetrakis(3-mercaptopropionate) is a common thiol monomer reacted with alkenes in the thiol-ene reaction to form polymeric networks. [3] Being functionalized with four thiol groups, it can react with multifunctional alkenes to form thiol-ene networks.
Diallyl carbonate is currently employed in the synthesis of the polymer through a thiol-ene reaction with dithiols. This component undergoes synthesis from hydroxamic acid and diallyl alcohol, with TBD catalyst facilitating the process. The outcome is a carbonaceous polymer characterized by high viscosity and transparency.
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Analogous reactions are known starting with Grignard reagents. Alternatively, sulfides can be synthesized by the addition of a thiol to an alkene in the thiol-ene reaction: R-CH=CH 2 + H-SR' → R-CH 2-CH 2-S-R' This reaction is often catalysed by free radicals produced from a photoinitiator. [6]