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Volumn 8, Issue 4, 2009, Pages 251-262

Thiol-ene chemistry of vinylsilanes

Author keywords

Thioether; Thiol ene; Vinylsilanes

Indexed keywords


EID: 75349105806     PISSN: 10241221     EISSN: 17451167     Source Type: Journal    
DOI: 10.1080/10241220903134411     Document Type: Review
Times cited : (19)

References (56)
  • 1
    • 84980124864 scopus 로고
    • Unsaturated Compounds. II. Mercaptan Addition to Unsaturated Hydrocarbons
    • T. Posner, Unsaturated Compounds. II. Mercaptan Addition to Unsaturated Hydrocarbons, Ber. Dtsch. Chem. Ges. 38, 646 (1905).
    • (1905) Ber. Dtsch. Chem. Ges , vol.38 , pp. 646
    • Posner, T.1
  • 2
    • 35948933962 scopus 로고    scopus 로고
    • Thiourethane-Based Thiol-Ene High Tg Networks: Preparation, Thermal, Mechanical, And Physical Properties
    • Q. Li, H. Zhou, D.A. Wicks and C.E. Hoyle, Thiourethane-Based Thiol-Ene High Tg Networks: Preparation, Thermal, Mechanical, And Physical Properties, J. Polym. Sci. Part A: Polym. Chem. 45, 5103 (2007).
    • (2007) J. Polym. Sci. Part A: Polym. Chem , vol.45 , pp. 5103
    • Li, Q.1    Zhou, H.2    Wicks, D.A.3    Hoyle, C.E.4
  • 3
  • 5
    • 54949090372 scopus 로고    scopus 로고
    • Highly Versatile and Robust Materials for Soft Imprint Lithography Based on Thiol-ene Click Chemistry
    • L.M. Campos, I. Meinel, R.G. Guino, M. Schierhorn, N. Gupta, G.D. Stucky and C.J. Hawker, Highly Versatile and Robust Materials for Soft Imprint Lithography Based on Thiol-ene Click Chemistry, Adv. Mater. 20, 3728 (2008).
    • (2008) Adv. Mater , vol.20 , pp. 3728
    • Campos, L.M.1    Meinel, I.2    Guino, R.G.3    Schierhorn, M.4    Gupta, N.5    Stucky, G.D.6    Hawker, C.J.7
  • 6
    • 56249095812 scopus 로고    scopus 로고
    • The Emergence of Thiol-ene Coupling as a Click Process for Materials and Bioorganic Chemistry
    • A. Dondoni, The Emergence of Thiol-ene Coupling as a Click Process for Materials and Bioorganic Chemistry, Angew. Chem. Int. Ed. 47, 8995 (2008).
    • (2008) Angew. Chem. Int. Ed , vol.47 , pp. 8995
    • Dondoni, A.1
  • 7
    • 36049017974 scopus 로고    scopus 로고
    • Thio-Click Modification of Poly[2-(3-butenyl)- 2-oxazoline]
    • A. Gress, A. Volkel and H. Schlaad, Thio-Click Modification of Poly[2-(3-butenyl)- 2-oxazoline], Macromolecules. 40, 7928 (2007).
    • (2007) Macromolecules , vol.40 , pp. 7928
    • Gress, A.1    Volkel, A.2    Schlaad, H.3
  • 8
    • 42149164860 scopus 로고    scopus 로고
    • Robust, Efficient, and Orthogonal Synthesis of Dendrimers via Thiol-ene ''Click'' Chemistry
    • K.L. Killops, L.M. Campos and C.J. Hawker. Robust, Efficient, and Orthogonal Synthesis of Dendrimers via Thiol-ene ''Click'' Chemistry, J. Am. Chem. Soc. 130, 5062 (2008).
    • (2008) J. Am. Chem. Soc , vol.130 , pp. 5062
    • Killops, K.L.1    Campos, L.M.2    Hawker, C.J.3
  • 9
    • 58349108839 scopus 로고    scopus 로고
    • Convergent Synthesis of 3-Arm Star Polymers from RAFT-Prepared Poly(N,N-diethylacrylamide) via a Thiol-Ene Click Reaction
    • J.W. Chan, B. Yu, C.E. Hoyle and A.B. Lowe, Convergent Synthesis of 3-Arm Star Polymers from RAFT-Prepared Poly(N,N-diethylacrylamide) via a Thiol-Ene Click Reaction, Chem. Commun. 4959 (2008).
    • (2008) Chem. Commun , pp. 4959
    • Chan, J.W.1    Yu, B.2    Hoyle, C.E.3    Lowe, A.B.4
  • 10
    • 65249177679 scopus 로고    scopus 로고
    • Stabilization and Functionalization of Polymer Multilayers and Capsules via Thiol-Ene Click Chemistry
    • L.A. Connal, C.R. Kinnane, A.N. Zelikin and F. Caruso, Stabilization and Functionalization of Polymer Multilayers and Capsules via Thiol-Ene Click Chemistry, Chem. Mater. 21, 576 (2009).
    • (2009) Chem. Mater , vol.21 , pp. 576
    • Connal, L.A.1    Kinnane, C.R.2    Zelikin, A.N.3    Caruso, F.4
  • 11
    • 60849097580 scopus 로고    scopus 로고
    • Synthesis of Thiol-Linked Neoglycopolymers and Thermo-Responsive Glycomicelles as Potential Drug Carrier
    • G. Chen, S. Amajjahe and M.H. Stenzel, Synthesis of Thiol-Linked Neoglycopolymers and Thermo-Responsive Glycomicelles as Potential Drug Carrier, Chem. Commun. 1198 (2009).
    • (2009) Chem. Commun , pp. 1198
    • Chen, G.1    Amajjahe, S.2    Stenzel, M.H.3
  • 12
    • 84981925786 scopus 로고
    • Problems and Possibilities of the Free-Radical Addition of Thiols to Unsaturated Compounds
    • K. Griesbaum, Problems and Possibilities of the Free-Radical Addition of Thiols to Unsaturated Compounds, Angew. Chem. Int. Ed. Engl. 9, 273 (1970).
    • (1970) Angew. Chem. Int. Ed. Engl , vol.9 , pp. 273
    • Griesbaum, K.1
  • 17
    • 33947452400 scopus 로고
    • Reaction of Mercaptans with Alkenyl Silanes
    • C.A. Burkhard, Reaction of Mercaptans with Alkenyl Silanes, J. Am. Chem. Soc. 72, 1078 (1950).
    • (1950) J. Am. Chem. Soc , vol.72 , pp. 1078
    • Burkhard, C.A.1
  • 18
    • 0010577797 scopus 로고
    • Peroxide Effect in the Addition of Reagents to Unsaturated Compounds. XVI. Styrene and Isobutylene
    • M.S. Kharasch, A.T. Read and F.R. Mayo, Peroxide Effect in the Addition of Reagents to Unsaturated Compounds. XVI. Styrene and Isobutylene, Chem. Ind. 52, 752 (1938).
    • (1938) Chem. Ind , vol.52 , pp. 752
    • Kharasch, M.S.1    Read, A.T.2    Mayo, F.R.3
  • 19
    • 0000817415 scopus 로고
    • The Peroxide Effect in the Addition of Reagents to Unsaturated Compounds and in Rearrangement Reactions
    • F.R. Mayo and C. Walling, The Peroxide Effect in the Addition of Reagents to Unsaturated Compounds and in Rearrangement Reactions, Chem. Rev. 27, 351 (1940).
    • (1940) Chem. Rev , vol.27 , pp. 351
    • Mayo, F.R.1    Walling, C.2
  • 20
    • 0011780808 scopus 로고
    • The Addition of Some Mercapto Compounds to a, b-Unsaturated Silanes
    • K. Wetterlin, The Addition of Some Mercapto Compounds to a, b-Unsaturated Silanes, Acta Chem. Scand. 18, 899 (1964).
    • (1964) Acta Chem. Scand , vol.18 , pp. 899
    • Wetterlin, K.1
  • 22
    • 0011785821 scopus 로고
    • Synthesis and Mass Spectra of o-(trimethylsilyl)alkyl Methyl Sulfides and Sulfones
    • T.I. Ito and W.P. Weber, Synthesis and Mass Spectra of o-(trimethylsilyl)alkyl Methyl Sulfides and Sulfones, J. Org. Chem. 39, 1694 (1974).
    • (1974) J. Org. Chem , vol.39 , pp. 1694
    • Ito, T.I.1    Weber, W.P.2
  • 23
    • 0001211941 scopus 로고
    • Practical Syntheses of Allylsilanes from 1-Benzenesulfonyl-2-trimethylsilylethane
    • C.N. Hsiao and H. Shecter, Practical Syntheses of Allylsilanes from 1-Benzenesulfonyl-2-trimethylsilylethane, Tetrahedron Lett. 23, 1963 (1982).
    • (1982) Tetrahedron Lett , vol.23 , pp. 1963
    • Hsiao, C.N.1    Shecter, H.2
  • 24
    • 0001544568 scopus 로고
    • Synthesis, Reactions, and Interconversions of Some 2-(trimethylsilyl) ethyl Substituted Sulfur Compounds
    • A.L. Schwan, D. Brillon and R. Dufault, Synthesis, Reactions, and Interconversions of Some 2-(trimethylsilyl) ethyl Substituted Sulfur Compounds, Can. J. Chem. 72, 325 (1994).
    • (1994) Can. J. Chem , vol.72 , pp. 325
    • Schwan, A.L.1    Brillon, D.2    Dufault, R.3
  • 26
    • 0001005901 scopus 로고
    • 1-Lithio-1-Benzenesulfinyl-2-trimethylsilylethane as a 2-Trimethylsilylvinyl Anion Equivalent in Reactions with Aldehydes, Ketones and Epoxides
    • C.N. Hsiao and H. Shechter, 1-Lithio-1-Benzenesulfinyl-2-trimethylsilylethane as a 2-Trimethylsilylvinyl Anion Equivalent in Reactions with Aldehydes, Ketones and Epoxides, Tetrahedron Lett. 24, 2371 (1983).
    • (1983) Tetrahedron Lett , vol.24 , pp. 2371
    • Hsiao, C.N.1    Shechter, H.2
  • 27
    • 0026631358 scopus 로고
    • The reaction of 2-Trimethylsilylethyl sulfoxides with Sulfuryl Chloride. A Fragmentation Route to Sulfinyl Chloride
    • A.L. Schwan and R. Dufault, The reaction of 2-Trimethylsilylethyl sulfoxides with Sulfuryl Chloride. A Fragmentation Route to Sulfinyl Chloride, Tetrahedron Lett. 33, 3973 (1992).
    • (1992) Tetrahedron Lett , vol.33 , pp. 3973
    • Schwan, A.L.1    Dufault, R.2
  • 28
    • 0028809041 scopus 로고
    • Asymmetric Chemical Oxidations of Aryl and alkyl 2-(trimethylsilyl)Ethyl Sulfides
    • A.L. Schwan and M.F. Pippert, Asymmetric Chemical Oxidations of Aryl and alkyl 2-(trimethylsilyl)Ethyl Sulfides, Tetrahedron: Asymmetry. 6, 131 (1995).
    • (1995) Tetrahedron: Asymmetry , vol.6 , pp. 131
    • Schwan, A.L.1    Pippert, M.F.2
  • 32
    • 27644502952 scopus 로고
    • Photochemical Addition of 2-Aminoethanethiol Hydrochloride and 2-(Diethylamino) ethanethiol to Triorgano(vinyl)- and Triorgano(ethynyl) silanes
    • G.Y. Zhila, O.G. Yarosh, N.N. Vlasova, A.I. Albanov and M.G. Voronkov, Photochemical Addition of 2-Aminoethanethiol Hydrochloride and 2-(Diethylamino) ethanethiol to Triorgano(vinyl)- and Triorgano(ethynyl) silanes, Zh. Obshch. Khim. 58, 536 (1988).
    • (1988) Zh. Obshch. Khim , vol.58 , pp. 536
    • Zhila, G.Y.1    Yarosh, O.G.2    Vlasova, N.N.3    Albanov, A.I.4    Voronkov, M.G.5
  • 33
  • 34
    • 0035034827 scopus 로고    scopus 로고
    • Oxidative Fragmentations of 2-(Trimethylsilyl)ethyl Sulfoxides - Routes to Alkane-, Arene-, and Highly Substituted 1-Alkenesulfinyl Chlorides
    • A.L. Schwan, R.R. Strickler, R. Dunn-Dufault and D. Brillon, Oxidative Fragmentations of 2-(Trimethylsilyl)ethyl Sulfoxides - Routes to Alkane-, Arene-, and Highly Substituted 1-Alkenesulfinyl Chlorides, Eur. J. Org. Chem. 2001, 1643 (2001).
    • (2001) Eur. J. Org. Chem , vol.2001 , pp. 1643
    • Schwan, A.L.1    Strickler, R.R.2    Dunn-Dufault, R.3    Brillon, D.4
  • 35
    • 0027972898 scopus 로고
    • Silver Fluoroborate Promoted Sulfur Alkylation of b-Silyl Ethyl Sulfides. Selective Synthesis of b-Thioglycosides
    • A. Mahadevan, C. Li and P.L. Fuchs, Silver Fluoroborate Promoted Sulfur Alkylation of b-Silyl Ethyl Sulfides. Selective Synthesis of b-Thioglycosides, Synth. Commun. 24, 3099 (1994).
    • (1994) Synth. Commun , vol.24 , pp. 3099
    • Mahadevan, A.1    Li, C.2    Fuchs, P.L.3
  • 36
    • 0005505291 scopus 로고
    • Unusual Reaction of [2-(trimethylsilyl) Ethylidene]triarylphosphoranes (Seyferth-Wittig reagent) with a-methyl Aldehydes: A Novel Method for Highly Cram-Diastereoselective Addition of Vinyl Anion Equivalent
    • M. Tsukamoto, H. Iio and T. Tokoroyama, Unusual Reaction of [2-(trimethylsilyl) Ethylidene]triarylphosphoranes (Seyferth-Wittig reagent) with a-methyl Aldehydes: a Novel Method for Highly Cram-Diastereoselective Addition of Vinyl Anion Equivalent, Tetrahedron Lett. 26, 4471 (1985).
    • (1985) Tetrahedron Lett , vol.26 , pp. 4471
    • Tsukamoto, M.1    Iio, H.2    Tokoroyama, T.3
  • 37
    • 0000651162 scopus 로고
    • Carbonyl Addition Reaction by Means of b-Silyl and b-Stannyl Phosphorus Ylides: Diastereoselective E-Propenylation of a-Chiral Aldehydes
    • M. Tsukamoto, H. Iio and T. Tokoroyama, Carbonyl Addition Reaction by Means of b-Silyl and b-Stannyl Phosphorus Ylides: Diastereoselective E-Propenylation of a-Chiral Aldehydes, Tetrahedron Lett. 28, 4561 (1987).
    • (1987) Tetrahedron Lett , vol.28 , pp. 4561
    • Tsukamoto, M.1    Iio, H.2    Tokoroyama, T.3
  • 38
    • 0025821027 scopus 로고
    • Enantioselective Vinylation of Aldehydes with Chiral b-Silylphosphorus Ylides
    • H. Iio, A. Fujii, M. Ishii and T. Tokoroyama, Enantioselective Vinylation of Aldehydes with Chiral b-Silylphosphorus Ylides, Chem. Commun. 1390 (1991).
    • (1991) Chem. Commun , pp. 1390
    • Iio, H.1    Fujii, A.2    Ishii, M.3    Tokoroyama, T.4
  • 39
    • 0028794549 scopus 로고    scopus 로고
    • 2-(Diphenylmethylsilyl) Ethyl Phenyl Sulfones as New Vinyl and Isopropenyl Anion Equivalents
    • A. Fujii, H. Iio and T. Tokoroyama, 2-(Diphenylmethylsilyl) Ethyl Phenyl Sulfones as New Vinyl and Isopropenyl Anion Equivalents, Synthesis. 1995, 78.
    • Synthesis , vol.1995 , pp. 78
    • Fujii, A.1    Iio, H.2    Tokoroyama, T.3
  • 40
    • 0001432317 scopus 로고    scopus 로고
    • Photocrosslinking of Silicones. Part 13. Photoinduced Thiol-Ene Crosslinking of Modified Silicones
    • U. Muller, A. Kunze, C. Herzig and J. Weis, Photocrosslinking of Silicones. Part 13. Photoinduced Thiol-Ene Crosslinking of Modified Silicones, J. Macromol. Sci. Chem. A. 33,439 (1996).
    • (1996) J. Macromol. Sci. Chem. A , vol.33 , pp. 439
    • Muller, U.1    Kunze, A.2    Herzig, C.3    Weis, J.4
  • 41
    • 0030574964 scopus 로고    scopus 로고
    • Controlled Synthesis of Siloxane Copolymers having an Organosulfur Group by Polymerization of Cyclotrisiloxanes with Mixed Units
    • K. Rozga-Wijas, J. Chojnowski, T. Zundel and S. Boileau, Controlled Synthesis of Siloxane Copolymers having an Organosulfur Group by Polymerization of Cyclotrisiloxanes with Mixed Units, Macromolecules. 29, 2711 (1996).
    • (1996) Macromolecules , vol.29 , pp. 2711
    • Rozga-Wijas, K.1    Chojnowski, J.2    Zundel, T.3    Boileau, S.4
  • 42
    • 0033667216 scopus 로고    scopus 로고
    • Controlled Synthesis of Amphiphilic Siloxane-Siloxane Block Copolymers with Carboxyl Functions
    • M. Scibiorek, N.K. Gladkova and J. Chojnowski, Controlled Synthesis of Amphiphilic Siloxane-Siloxane Block Copolymers with Carboxyl Functions, Polym. Bull. 44, 377 (2000).
    • (2000) Polym. Bull , vol.44 , pp. 377
    • Scibiorek, M.1    Gladkova, N.K.2    Chojnowski, J.3
  • 43
    • 0001403646 scopus 로고    scopus 로고
    • Modification of Polysiloxanes by Free-Radical Addition of Pyridylthiols to the Vinyl Groups of the Polymer
    • L. Herczynska, L. Lestel, S. Boileau, J. Chojnowski and S. Polowinski, Modification of Polysiloxanes by Free-Radical Addition of Pyridylthiols to the Vinyl Groups of the Polymer, Eur. Polym. J. 35, 1115 (1999).
    • (1999) Eur. Polym. J , vol.35 , pp. 1115
    • Herczynska, L.1    Lestel, L.2    Boileau, S.3    Chojnowski, J.4    Polowinski, S.5
  • 45
    • 33947164219 scopus 로고    scopus 로고
    • Field-Induced Motion of Ferrofluids Through Immiscible Viscous Media: Testbed for Restorative Treatment of Retinal Detachment
    • O.T. Mefford, R.C. Woodward, J.D. Goff, T.P. Vadala, T.G. St. Pierre, J.P. Dailey and J.S. Riffle, Field-Induced Motion of Ferrofluids Through Immiscible Viscous Media: Testbed for Restorative Treatment of Retinal Detachment, J. Magn. Magn. Mater. 311, 347 (2007).
    • (2007) J. Magn. Magn. Mater , vol.311 , pp. 347
    • Mefford, O.T.1    Woodward, R.C.2    Goff, J.D.3    Vadala, T.P.4    St. Pierre, T.G.5    Dailey, J.P.6    Riffle, J.S.7
  • 46
    • 34547807820 scopus 로고    scopus 로고
    • Synthesis and Characterization of Hyperbranched Poly(siloxysilane) Possessing Rhodamine B as Terminal Group
    • L. Ding, T. Hayakawa and M.-A. Kakimoto, Synthesis and Characterization of Hyperbranched Poly(siloxysilane) Possessing Rhodamine B as Terminal Group, Polym. J. 39, 551 (2007).
    • (2007) Polym. J , vol.39 , pp. 551
    • Ding, L.1    Hayakawa, T.2    Kakimoto, M.-A.3
  • 47
    • 51849122525 scopus 로고    scopus 로고
    • Synthesis and Characterization of Photoplastic Siloxane Based Thiol-Ene Polymer Systems
    • S.N. Pawar and T.W. Smith, Synthesis and Characterization of Photoplastic Siloxane Based Thiol-Ene Polymer Systems, Polym. Prepr. 49, 1079 (2008).
    • (2008) Polym. Prepr , vol.49 , pp. 1079
    • Pawar, S.N.1    Smith, T.W.2
  • 49
    • 6444228838 scopus 로고    scopus 로고
    • Efficient Preparation of Glycoclusters from Silsesquioxanes
    • Y. Gao, A. Eguchi, K. Kakehi and Y.C. Lee, Efficient Preparation of Glycoclusters from Silsesquioxanes, Org. Lett. 6, 3457 (2004).
    • (2004) Org. Lett , vol.6 , pp. 3457
    • Gao, Y.1    Eguchi, A.2    Kakehi, K.3    Lee, Y.C.4
  • 50
    • 18344386171 scopus 로고    scopus 로고
    • Poly(amidoamine-organosilicon) (PAMAMOS) Multi-Arm Star Polymers
    • P.R. Dvornic, J. Hu, S.D. Reeves and M.J. Owen, Poly(amidoamine-organosilicon) (PAMAMOS) Multi-Arm Star Polymers, Silicon Chem. 1, 177 (2002).
    • (2002) Silicon Chem , vol.1 , pp. 177
    • Dvornic, P.R.1    Hu, J.2    Reeves, S.D.3    Owen, M.J.4
  • 51
    • 0001924597 scopus 로고    scopus 로고
    • Silicon-Based Dendrimers
    • H. Frey and C. Schlenk, Silicon-Based Dendrimers, Top. Curr. Chem. 210, 69 (2000).
    • (2000) Top. Curr. Chem , vol.210 , pp. 69
    • Frey, H.1    Schlenk, C.2
  • 52
    • 0003670973 scopus 로고    scopus 로고
    • edited by Z. Rappoport and Y. Apeloig, John Wiley & Sons, New York
    • D.Y. Son, in The Chemistry of Organic Silicon Compounds, edited by Z. Rappoport and Y. Apeloig (John Wiley & Sons, New York, 2001).
    • (2001) The Chemistry of Organic Silicon Compounds
    • Son, D.Y.1
  • 55
    • 55249096054 scopus 로고    scopus 로고
    • Thiol-Ene Reaction for the Synthesis of Multifunctional Branched Organosilanes
    • C. Rissing and D.Y. Son, Thiol-Ene Reaction for the Synthesis of Multifunctional Branched Organosilanes, Organometallics. 27, 5394 (2008).
    • (2008) Organometallics , vol.27 , pp. 5394
    • Rissing, C.1    Son, D.Y.2
  • 56
    • 66349103061 scopus 로고    scopus 로고
    • Application of Thiol-Ene Chemistry to the Preparation of Carbosilane-Thioether Dendrimers
    • C. Rissing and D.Y. Son, Application of Thiol-Ene Chemistry to the Preparation of Carbosilane-Thioether Dendrimers, Organometallics. 28, 3167 (2009).
    • (2009) Organometallics , vol.28 , pp. 3167
    • Rissing, C.1    Son, D.Y.2


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