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Formation of a thioether (–S–) compound from a thiol (–SH) and an alkene ( >C=C< )
In organosulfur chemistry, the thiol-ene reaction (also alkene hydrothiolation) is an organic reaction between a thiol (R−SH) and an alkene (R2C=CR2)
Thiol-ene_reaction
Reaction in organic chemistry
organic chemistry, the ene reaction (also known as the Alder-ene reaction by its discoverer Kurt Alder in 1943) is a chemical reaction between a relatively
Ene_reaction
Chemical addition of an –SH and –C≡CH molecule
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
Thiol-yne_reaction
Chemical compound
the 2-norbornyl cation. Being a strained ene, norbornenes react readily with thiols in the thiol-ene reaction to form thioethers. This makes norbornene-functionalized
Norbornene
Topics referred to by the same term
involved in the Ene reaction and the Thiol-ene reaction -ene, a suffix used in the names of certain organic compounds (alkenes) Ene, Spanish abbreviation
Ene
off-stoichiometry thiol-ene polymer is a polymer platform comprising off-stoichiometry thiol-enes (OSTE) and off-stoichiometry thiol-ene-epoxies (OSTE+)
Off-stoichiometry thiol-ene polymer
Off-stoichiometry_thiol-ene_polymer
Class of chemical compounds
readily with thiols in the thiol-ene reaction to form thioethers. This makes enol ether-functionalized monomers ideal for polymerization with thiol-based monomers
Enol_ether
Chemical compound
moiety in the thiol-ene reaction, nadic anhydride is used in the synthesis of monomers for cross-linked polymer networks based on thiol-ene linkages. Nadic
Nadic_anhydride
Chemical compound
attach to surfaces, and can prepare nanocomposite materials via thiol-ene reactions. These polymerizations are often initiated with UV reactive photoinitiators
(3-Mercaptopropyl)trimethoxysilane
(3-Mercaptopropyl)trimethoxysilane
Chemical compound
is a common thiol monomer reacted with alkenes in the thiol-ene reaction to form polymeric networks. Being functionalized with four thiol groups, it can
Pentaerythritol tetrakis(3-mercaptopropionate)
Pentaerythritol_tetrakis(3-mercaptopropionate)
Transfer of an alkyl group from one molecule to another
products being phosphonium salts. Thiols are readily alkylated to give thioethers via the thiol-ene reaction. The reaction is typically conducted in the presence
Alkylation
Organic compound with an –S– group
15227/orgsyn.058.0143. Hoyle, Charles E.; Bowman, Christopher N. (2010-02-22). "Thiol-Ene Click Chemistry". Angewandte Chemie International Edition. 49 (9): 1540–1573
Organic_sulfide
The main reaction of thiyl radicals their reversion to disulfides: 2 RS· → RS−SR Thiyl radicals are intermediates in the thiol-ene reaction, which is
Thiyl_radical
Chemical reaction
The Mitsunobu reaction is an organic reaction that converts an alcohol into a variety of functional groups, such as an ester, using triphenylphosphine
Mitsunobu_reaction
Chemical compound
reduction of a typical disulfide bond proceeds by two sequential thiol-disulfide exchange reactions and is illustrated below. The reduction usually does not stop
Dithiothreitol
Chemical compound
1021/ja0315199. PMID 15080700. Hoyle, Charles E.; Bowman, Christopher N. (2010). "Thiol–Ene Click Chemistry". Angewandte Chemie International Edition. 49 (9): 1542–1543
3-Mercaptopropionic_acid
Organic addition reaction which involves free radicals
hydrogen. In general, these reactions risk polymerized byproducts (see § Side reactions). For example, in the thiol-ene reaction, thiols, disulfides, and hydrogen
Free-radical_addition
Acrylating agent
carbonate is currently employed in the synthesis of the polymer through a thiol-ene reaction with dithiols. This component undergoes synthesis from hydroxamic
Diallyl_carbonate
Plastics derived from renewable biomass sources
resin from vegetable oils: From the synthesis of the precursors by thiol-ene reaction to the study of the final material" (PDF). Journal of Polymer Science
Bioplastic
reaction Alcohol oxidation Alder ene reaction Alder–Stein rules Aldol addition Aldol condensation Algar–Flynn–Oyamada reaction Alkylimino-de-oxo-bisubstitution
List_of_organic_reactions
American organic materials chemist
Hawker on functionalization and cross-linking of polymers using the thiol-ene reaction. Campos has started his independent academic career in 2011 as an
Luis_M._Campos
Chemical compound
sulfur-containing amino acids, such as cysteine, to create 3-methylbut-2-ene-1-thiol, a thiol which causes beer to develop a "skunky" flavor. Isohumulones are
Isohumulone
Hydrocarbon compound containing one or more C≡C bonds
oxidize to the corresponding aldehyde or ketone. In the thiol-yne reaction the adding reagent is a thiol. Depending on catalysts and conditions, alkynes are
Alkyne
Chemical reactions involving organic compounds
place is much smaller, for example the ene reaction or aldol reaction. Another approach to organic reactions is by type of organic reagent, many of them
Organic_reaction
Hydrocarbon compound containing one or more C=C bonds
via rearrangement reactions. Besides olefin metathesis (described above), many pericyclic reactions can be used such as the ene reaction and the Cope rearrangement
Alkene
Modular approach to chemical synthesis
preceramic polymers: A versatile stereolithographic approach assisted by thiol-ene click chemistry". Additive Manufacturing. 27: 80–90. arXiv:1905.02060
Click_chemistry
Chemical compound
main source of reactivity being the double bonds. These can undergo thiol-ene reactions, forming botryococcene pentathiolate under UV radiation, or hydrogenation
Botryococcenes
Chemical compound
activity can be attributed to both its antioxidant activity and its reaction with thiol-containing proteins. Allicin features the thiosulfinate functional
Allicin
preceramic polymers: A versatile stereolithographic approach assisted by thiol-ene click chemistry, Additive Manufacturing 2019, volume 27 pages 80-90
Polysilane
Chemical compound
Spessard, Gary O.; Chan, Wan Kit; Masamune, S. (1983). "Preparation of thiol esters: S-tert-butyl cyclohexanecarbothioate and S-tert-butyl 3α,7α
Cyclohexanecarboxylic_acid
Chemical compound
1021/cr60134a004. PMID 18876970. Hoyle, Charles E.; Bowman, Christopher N. (2010). "Thiol–Ene Click Chemistry". Angewandte Chemie International Edition. 49 (9): 1542–1543
Pentaerythritol
Chemical compound
OND) display unusually high reactivity towards organic azides and thiols. OND–thiol adducts are prone to retro-Diels–Alder fragmentation, which occurs
Oxanorbornadiene
Russian organic chemist
Alexander D. (2019-06-21). "Visible-Light-Mediated Organocatalyzed Thiol–Ene Reaction Initiated by a Proton-Coupled Electron Transfer". The Journal of Organic
Alexander_Dilman
Chemical compound
pubchem.ncbi.nlm.nih.gov. Türünç, Oĝuz; Meier, Michael A. R. (2011). "Thiol-ene vs. ADMET: a complementary approach to fatty acid-based biodegradable
1,4-Butanedithiol
are prepared by reaction of alkali metal salts of 1,2-alkenedithiolates with metal halides. A thiolate is the conjugate base of a thiol, so alkenedithiolate
Metal_dithiolene_complex
Chemical compound
amines, and thiols. One methyl group is transferred more quickly than the second. Methyl transfer is assumed to occur via an SN2 reaction. Compared to
Dimethyl_sulfate
Chemical compound
aldehydes, thiols to disulfides and hydrazo groups to azo groups. It also undergoes pericyclic reactions with alkenes and dienes via ene and Diels–Alder
Diethyl_azodicarboxylate
Light-sensitive material used in making electronics
allowed for the higher photon energy. The absorbed energy can drive further reactions and ultimately dissipates as heat. This is associated with the outgassing
Photoresist
Class of chemical compounds
are produced by autoxidation, the direct reaction of O2 with a hydrocarbon. Autoxidation is a radical reaction that begins with the abstraction of an H
Hydroperoxide
Anders; et al. (2010). "Accelerated Growth of Dendrimers via Thiol−Ene and Esterification Reactions". Macromolecules. 43 (14): 6004. Bibcode:2010MaMol..43.6004M
Polymer_Factory_Sweden_AB
Class of functional groups with a –N=O group attached
synthesis, Bartoli indole synthesis. In the Saville reaction, mercury is used to replace a nitrosyl from a thiol group. C-nitroso compounds are used in organic
Nitroso
Stereogenic group placed on a molecule to encourage stereoselectivity in reactions
Whitesell and coworkers in 1985. This chiral auxiliary was used in ene reactions of the derived ester of glyoxylic acid. In the total synthesis of (−)-heptemerone
Chiral_auxiliary
Chemical compound
with diazomethane, the six-membered ring is closed by reaction with 1,5-diazabicyclo[5.4.0]undec-5-ene (DBU), and the ester protection is removed with trifluoroacetic
Cefroxadine
quaternization of C1, C3, C4-substituted imidazole and crosslinking them via "thiol-ene" chemistry. These crosslinked AEMs showed excellent film forming properties
Alkaline anion-exchange membrane fuel cell
Alkaline_anion-exchange_membrane_fuel_cell
Functional group of organic compounds
electrophiles in the body. Some drugs (amifostine, N-acetylcysteine) containing thiol groups may protect from such harmful alkylation. 2-alkenal reductase Dicarbonyls
Α,β-Unsaturated carbonyl compound
Α,β-Unsaturated_carbonyl_compound
Chemical reaction run in a continuous stream
Junkers, Thomas (August 2012). "Use of a continuous-flow microreactor for thiol–ene functionalization of RAFT-derived poly(butyl acrylate)". Polym. Chem.
Flow_chemistry
Chemical group (–CH2–CH=CH2)
reactivity. Other reactions that tend to occur with allylic compounds are selenoxide oxidations, ene reactions, and the Tsuji–Trost reaction. Benzylic groups
Allyl_group
Chemical compound
The chemical synthesis was described: Patent: Ketalization of Estr-5(10)-ene-3,17-dione [3962-66-1] (1) with two equivalents of ethylene glycol gives
Plomestane
Chemical group (–C4H9) derived from butane
syntheses of optically active 19-nor steroids. (+)-Estr-4-ene-3,17-dione and (+)-13.beta.-ethylgon-4-ene-3,17-dione". The Journal of Organic Chemistry. 40 (6):
Butyl_group
American synthetic chemist
system, Brummond uses an allenic Pauson–Khand reactions and other cyclization process. To regulate the thiol reactivity and increase affinity for the kinase
Kay_Brummond
Resin that cures when exposed to light of appropriate wavelengths
preceramic polymers: A versatile stereolithographic approach assisted by thiol-ene click chemistry". Additive Manufacturing. 27: 80–90. arXiv:1905.02060
Photopolymer
Highly ordered, branched polymeric molecule
click chemistry, employing Diels-Alder reactions, thiol-ene and thiol-yne reactions and azide-alkyne reactions. There are ample avenues that can be opened
Dendrimer
Family of polymers
preceramic polymers A versatile stereolithographic approach assisted by thiol–ene click chemistry" (PDF). Additive Manufacturing. 27: 80–90. 2019. Du, Boxue
Silicone
Hydrocarbon compound (H2C=CH2)
the first member.[citation needed] In the mid-19th century, the suffix -ene (an Ancient Greek root added to the end of female names meaning "daughter
Ethylene
Device for tracking proteins
detection; however, they do offer much promise for the future. Immunoassays on thiol-ene "synthetic paper" micropillar scaffolds have shown to generate a superior
Protein_microarray
Main-group allene analog
to the success of these reactions. The dehydrochlorination of 1-chlorovinylphosphine by DBU (1,8-diazabicyclo-[5.4.0]undec-7-ene) yields a variety of results
1-Phosphaallenes
Class of extremely unreactive, inert and fire-resistant polymers
alignment, but also diamagnetic, dielectric, surface alignment. For example, thiol-ene radical step-growth polymerization and Michael addition produce well-ordered
Liquid-crystal_polymer
Lithographic technique that uses a scanning beam of electrons
silicon but not silicon dioxide or other similar dielectrics. In 2018, a thiol-ene resist was developed that features native reactive surface groups, which
Electron-beam_lithography
Study of chemical compounds containing carbon-selenium bonds
about this reaction. In terms of reaction mechanism, SeO2 and the allylic substrate react via pericyclic process beginning with an ene reaction that activates
Organoselenium_chemistry
Composite material consisting of ceramic fibers in a ceramic matrix
preceramic polymers: A versatile stereolithographic approach assisted by thiol-ene click chemistry, Additive Manufacturing 2019, volume 27 pages 80-90 G
Ceramic_matrix_composite
Type of saturated hydrocarbon compound
the whole sequence of vowels a, e, i, o and u to create suffixes -ane, -ene, -ine (or -yne), -one, -une, for the hydrocarbons CnH2n+2, CnH2n, CnH2n−2
Alkane
Compound of silicon and nitrogen
preceramic polymers: A versatile stereolithographic approach assisted by thiol-ene click chemistry". Additive Manufacturing. 27: 80–90. arXiv:1905.02060
Silicon_nitride
Chemical compound
radical, which in the 4-position adds phenols, as well as alcohols and thiols to the corresponding cyclohexadienones. The cyclohexadienones, also referred
2,4,6-Tri-tert-butylphenol
Thermal decomposition of materials
preceramic polymers: A versatile stereolithographic approach assisted by thiol-ene click chemistry". Additive Manufacturing. 27: 80–90. arXiv:1905.02060
Pyrolysis
Class of organic compounds
(water-attracted) properties. The OH group provides a site at which many reactions can occur. The flammable nature of the exhalations of wine was already
Alcohol_(chemistry)
Emerging technology field
nanoscale size, for example DNA, proteins or nanostructured mechanical parts. Thiol-ene e-beams resist allow the direct writing of nanoscale features, followed
Nanorobotics
Method of fabricating nanometer scale patterns using a special stamp
and suffer from structural collapse. Using UV-NIL of off-stoichiometric thiol–ene-epoxy polymer it is possible to fabricate robust, large-area, and high-aspect-ratio
Nanoimprint_lithography
Group of atoms giving a molecule characteristic properties
molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest of the molecule's
Functional_group
Wide-bandgap semiconductor and abrasion-resistant ceramic
preceramic polymers: A versatile stereolithographic approach assisted by thiol-ene click chemistry". Additive Manufacturing. 27: 80–90. arXiv:1905.02060
Silicon_carbide
Chemical compound
molecule. Its mechanism of action induces a Pinner reaction which is initiated by reacting with thiols, alcohols and amines. Thus, leading to the formation
Dapansutrile
Chemical compound
toward nucleophiles, e.g. methanol. It also forms addition compounds with thiols, and it is this reactivity that may be related to its toxicity. It hydrolyzes
Perfluoroisobutene
Class of positively-charged molecules
hydrogen sulfide) Organic derivatives can be primary (H2SR+, protonated thiols), secondary (HSR+2, protonated thioethers), or ternary (SR+3, e.g. trimethylsulfonium)
Onium_ion
Glass type
preceramic polymers: A versatile stereolithographic approach assisted by thiol-ene click chemistry". Additive Manufacturing. 27: 80–90. arXiv:1905.02060
Oxycarbide_glass
Chemical compound
epoxide is opened at the least hindered end with 1-methyl-1H-tetrazole-5-thiol to put in place the future C-3 side chain and give intermediate 5. Jones
Latamoxef
Device integrating laboratory functions on an integrated circuit
polydimethylsiloxane (PDMS) processing (e.g., soft lithography), Off-stoichiometry thiol-ene polymers (OSTEmer) processing, thick-film- and stereolithography-based
Lab-on-a-chip
Chemical compound
and thiohydroxamines may be formed from their corresponding alcohols and thiols, sulfimides may be formed from thioethers and α-aminoketones may be formed
Oxaziridine
Chemical compound
bond undergoing reduction within the cell to release a zinc-binding thiol. The thiol binds to a zinc atom in the binding pocket of Zn-dependent histone
Romidepsin
Anti-cancer drug
DNA, the epoxide is activated in one of two ways. First, if NADPH or a thiol reduces the molecule the Bergman re-cyclization of the enediyne proceeds
Dynemicin_A
Any organic compound containing one double and two triple bonds
inactive esperamicin naturally produced by A. verrucosospora. Compounds with thiol groups induce triggering among the esperamicins. The dynemicins are a sub-family
Enediyne
Protein-coding gene in the species Homo sapiens
isomerization of hemithioacetal adducts, which are formed in a spontaneous reaction between a glutathionyl group and aldehydes such as methylglyoxal.
Lactoylglutathione_lyase
Type of water-resistant material from plants
"Newly UV-curable polyurethane coatings prepared by multifunctional thiol- and ene-terminated polyurethane aqueous dispersions: Photopolymerization properties"
Waterborne_resin
American chemist
Alexander K.; Farrell, Richard A.; Garrell, Robin L. (5 July 2011). "Thiol–ene Click Reaction as a General Route to Functional Trialkoxysilanes for Surface Coating
Robin_L._Garrell
Steroidal antiandrogen and antimineralocorticoid
7α-TS is also S-methylated into 7α-TMS, a transformation catalyzed by thiol S-methyltransferase. Unlike the related medication eplerenone, spironolactone
Spironolactone
8.2.7: thiocyanate desulfurase EC 1.8.3.1: sulfite oxidase EC 1.8.3.2: thiol oxidase EC 1.8.3.3: glutathione oxidase EC 1.8.3.4: methanethiol oxidase
List_of_EC_numbers_(EC_1)
Czech-American chemist (born 1940)
Reversible Addition-Fragmentation Chain Transfer Polymerization and Thiol-ene Coupling Reaction". Biomacromolecules 12, 247–252 (2011) K. Wu, J. Liu, R.N. Johnson
Jindřich_Kopeček
Dutch scientist
Tessa; Calore, Andrea; Moroni, Lorenzo; Baker, Matthew B. (25 June 2018). "ThiolEne Alginate Hydrogels as Versatile Bioinks for Bioprinting". Biomacromolecules
Clemens_van_Blitterswijk
Austrian professor of organic chemistry (born 1939)
Pocket as a Reaction Vessel in Bile Pigment Chemistry. Monatsh. Chem. 121, 903 (1990) H. Falk und H. Marko, Reduction of a Bilindione-10-Thiol-Adduct as
Heinz_Falk
Berger, François; Delhalle, Joseph; Mekhalif, Zineb (2009). "Undec-10-ene-1-thiol multifunctional molecular layer as a junction between metallic zinc and
Scanning vibrating electrode technique
Scanning_vibrating_electrode_technique
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THIOL ENE-REACTION
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