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Thiol-ene reactions are known to proceed through a Michael addition pathway. These reactions are catalyzed by either a base or a nucleophile, resulting in a similar anti-Markovnikov addition product as the thiol-ene radical addition.
Others, however, insist that such a usage is an abuse of terminology, and limit the Michael addition to the formation of carbon–carbon bonds through the addition of carbon nucleophiles. The terms oxa-Michael reaction and aza-Michael reaction [2] have been used to refer to the 1,4-addition of oxygen and nitrogen nucleophiles, respectively. The ...
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.
Thiol-ene reaction [7] [8] Diels ... and phenyl azide, was reported by Arthur Michael in ... reaction is another dipolar addition that Huisgen first introduced in the ...
NEM is a Michael acceptor in the Michael reaction, which means that it adds nucleophiles such as thiols. The resulting thioether features a strong C–S bond and the reaction is virtually irreversible. Reaction with thiols occur in the pH range 6.5–7.5, NEM may react with amines or undergo hydrolysis at a more alkaline pH.
In organic chemistry, the thiol-yne reaction (also known as alkyne hydrothiolation) is an organic reaction between a thiol (−SH) and an alkyne (−C≡CH). The reaction product is an alkenyl sulfide (−CH=CH−S−). [1] [2] The reaction was first reported in 1949 with thioacetic acid as reagent [3] [4] and rediscovered in 2009. [5]
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] Sulfides can also be prepared by many other methods, such as the Pummerer rearrangement. Trialkysulfonium salts ...
In a free-radical addition, there are two chain propagation steps. In one, the adding radical attaches to a multiply-bonded precursor to give a radical with lesser bond order. In the other, the newly-formed radical product abstracts another substituent from the adding reagent to regenerate the adding radical. [3]: 743–744