507
Views
3
CrossRef citations to date
0
Altmetric
Articles

Reversible oligomerization of 3-aryl-2-cyanothioacrylamides via [2s + 4s] cycloaddition to substituted 3,4-dihydro-2H-thiopyrans

, , , , &
Pages 627-640 | Received 26 Feb 2015, Accepted 19 May 2015, Published online: 09 Jul 2015

References

  • Goussé C, Gandini A, Hodge P. Application of the Diels−Alder reaction to polymers bearing furan moieties. 2. Diels−Alder and retro-Diels−Alder reactions involving furan rings in some styrene copolymers. Macromolecules. 1998;31:314–321.10.1021/ma9710141
  • Murphy EB, Bolanos E, Schaffner-Hamann C, Wudl F, Nutt SR, Auad ML. Synthesis and characterization of a single-component thermally remendable polymer network: Staudinger and Stille revisited. Macromolecules. 2008;41:5203–5209.10.1021/ma800432g
  • Peterson AM, Jensen RE, Palmese GR. Room-temperature healing of a thermosetting polymer using the Diels−Alder reaction. ACS Appl. Mater. Interfaces. 2010;2:1141–1149.10.1021/am9009378
  • Bergman SD, Wudl F. Mendable polymers. J. Mater. Chem. 2007;18:41–62.
  • Hager MD, Greil P, Leyens C, van der Zwaag S, Schubert US. Self-healing materials. Adv. Mater. 2010;22:5424–5430.10.1002/adma.201003036
  • Chen X, Dam MA, Ono K, et al. A thermally re-mendable cross-linked polymeric material. Science. 2002;295:1698–1702.10.1126/science.1065879
  • Chen X, Wudl F, Mal AK, Shen H, Nutt SR. New thermally remendable highly cross-linked polymeric materials. Macromolecules. 2003;36:1802–1807.10.1021/ma0210675
  • Sinnwell S, Inglis AJ, Davis TP, Stenzel MH, Barner-Kowollik C. An atom-efficient conjugation approach to well-defined block copolymers using RAFT chemistry and hetero Diels-Alder cycloaddition. Chem. Commun. 2008;2052–2054.10.1039/b718180a
  • Inglis AJ, Nebhani L, Altintas O, Schmidt FG, Barner-Kowollik C. Rapid bonding/debonding on demand: reversibly cross-linked functional polymers via Diels−Alder chemistry. Macromolecules. 2010;43:5515–5520.10.1021/ma100945b
  • Paulöhrl T, Inglis AJ, Barner-Kowollik C. Reversible Diels-Alder chemistry as a modular polymeric color switch. Adv. Mater. 2010;22:2788–2791.10.1002/adma.201000361
  • Espinosa E, Glassner M, Boisson C, Barner-Kowollik C, D'Agosto F. Synthesis of cyclopentadienyl capped polyethylene and subsequent block copolymer formation via hetero Diels-Alder (HDA) Chemistry. Macromol. Rapid Commun. 2011;32:1447–1453.10.1002/marc.v32.18
  • Brandt J, Guimard NK, Barner-Kowollik C, Schmidt FG, Lederer A. Temperature-dependent size exclusion chromatography for the in situ investigation of dynamic bonding/debonding reactions. Anal. Bioanal. Chem. 2013;405:8981–8993.10.1007/s00216-013-7203-8
  • Guimard NK, Ho J, Brandt J, et al. Harnessing entropy to direct the bonding/debonding of polymer systems based on reversible chemistry. Chem. Sci. 2013;4:2752–2759.10.1039/c3sc50642h
  • Oehlenschlaeger KK, Guimard NK, Brandt J, et al. Fast and catalyst-free hetero-Diels–Alder chemistry for on demand cyclable bonding/debonding materials. Polym. Chem. 2013;4:4348–4355.10.1039/c3py00476g
  • Pahnke K, Brandt JGryn’ova G, et al. Entropy driven chain effects on ligation chemistry. Chem. Sci. 2015;6:1061–1074.
  • Inglis AJ, Sinnwell S, Stenzel MH, Barner-Kowollik C. Ultrafast click conjugation of macromolecular building blocks at ambient temperature. Angew. Chem. Int. Ed. Engl. 2009;48:2411–2414.10.1002/anie.200805993
  • Inglis AJ, Stenzel MH, Barner-Kowollik C. Ultra-fast RAFT-HDA click conjugation: an efficient route to high molecular weight block copolymers. Macromol. Rapid Commun. 2009;30:1792–1798.10.1002/marc.v30:21
  • Langer M, Brandt J, Lederer A, Goldmann AS, Schacher FH, Barner-Kowollik C. Amphiphilic block copolymers featuring a reversible hetero Diels-Alder linkage. Polym. Chem. 2014;5:5330–5338.10.1039/C4PY00644E
  • Oehlenschlaeger KK, Mueller JO, Brandt J, et al. Adaptable hetero Diels–Alder networks for fast self-healing under mild conditions. Adv. Mater. 2014;26:3561–3566.10.1002/adma.v26.21
  • Boul PJ, Reutenauer P, Lehn J. Reversible Diels−Alder reactions for the generation of dynamic combinatorial libraries. Org. Lett. 2005;7:15–18.10.1021/ol048065k
  • Reutenauer P, Buhler E, Boul PJ, Candau SJ, Lehn J. Room temperature dynamic polymers based on Diels-Alder chemistry. Chem. Eur. J. 2009;15:1893–1900.10.1002/chem.v15:8
  • Reutenauer P, Boul PJ, Lehn J. Dynamic Diels-Alder reactions of 9,10-dimethylanthracene: reversible adduct formation, dynamic exchange processes and thermal fluorescence modulation. Eur. J. Org. Chem. 2009;2009:1691–1697.10.1002/ejoc.v2009:11
  • Brunskill JSA, De A, Ewing DF. Dimerisation of 3-aryl-2-cyanothioacrylamides. A [2s+ 4s] cyclo-addition to give substituted 3,4-dihydro-2H-thiopyrans. J. Chem. Soc., Perkin Trans. 1. 1978:629–633.10.1039/p19780000629
  • Brunskill JSA, De A, Ewing DF. Substituent effects on a reversible cycloaddition reaction. J. Chem. Soc., Perkin Trans. 2. 1980:4.
  • Bloxham J, Dell CP. Reaction of 3-aryl-2-cyanothioacrylamides with electron-deficient alkynes: synthesis of 4-aryl-4H-thiopyrans. J. Chem. Soc., Perkin Trans. 1. 1994:989–993.10.1039/p19940000989
  • Kerszulis JA, Amb CM, Dyer AL, Reynolds JR. Follow the yellow brick road: structural optimization of vibrant yellow-to-transmissive electrochromic conjugated polymers. Macromolecules. 2014;47:5462–5469.10.1021/ma501080u
  • Piñol R, Lub J, García MP, et al. Synthesis, properties, and polymerization of new liquid crystalline monomers for highly ordered guest−host systems. Chem. Mater. 2008;20:6076–6086.
  • Ransborg LK, Albrecht Ł, Weise CF, Bak JR, Jørgensen KA. Optically active thiophenes via an organocatalytic one-pot methodology. Org. Lett. 2012;14:724–727.10.1021/ol203237r
  • Aboutabl MA, Abdel Aziz MA, Magd El Din AA, Elwy HA, Fahmy HM. Electrochemical reduction of some 3-aryl-2-cyanothioacrylamide derivatives at the DME. Monatsh. Chem. 1991;122:765–770.10.1007/BF00815916
  • Di Marco VB, Bombi GG. Electrospray mass spectrometry (ESI-MS) in the study of metal-ligand solution equilibria. Mass. Spectrom. Rev. 2006;25:347–379.10.1002/(ISSN)1098-2787
  • Schug K, McNair HM. Adduct formation in electrospray ionization mass spectrometry. J. Chromatogr. A. 2003;985:531–539.10.1016/S0021-9673(02)01732-6
  • Motoki S, Saito T, Karakasa T, et al. Lewis acid-promoted hetero Diels-Alder reaction of α, β-unsaturated thioketones. J. Chem. Soc., Perkin Trans. 1. 1992:2943–2948.10.1039/p19920002943
  • Saito T, Fujii H, Hayashibe S, Matsushita T, Kato H, Kobayashi K. Uncatalysed (thermal) and Lewis acid-promoted asymmetric hetero-Diels–Alder reaction of 1-thiabuta-1,3-dienes (thiochalcones) with di-(–)-menthyl fumarate. Configuration determination by x-ray crystallographic analysis of (2s,3r,4r)-(+)-2,3-bis[(–)-menthoxycarbonyl]-4,6-diphenyl-3,4-dihydro-2h-thiopyran and conversion of cycloadducts into optically pure diols. J. Chem. Soc., Perkin Trans. 1. 1996:1897–1903.10.1039/p19960001897
  • Bastin R, Albadri H, Gaumont A, Gulea M. Pyridinedithioesters as heterodienophiles: application to the synthesis of Aprikalim. Org. Lett. 2006;8:1033–1036.10.1021/ol052942k
  • Zhou J, Guimard NK, Inglis AJ, et al. Thermally reversible Diels–Alder-based polymerization: an experimental and theoretical assessment. Polym. Chem. 2012;3:628–639.
  • Kryuchkov MA, Detrembleur C, Jérôme R, Prud’homme RE, Bazuin CG. Synthesis and thermal properties of linear amphiphilic diblock copolymers of L-lactide and 2-dimethylaminoethyl methacrylate. Macromolecules. 2011;44:5209–5217.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.