Cascade Ring Strain Release Polymerization of Cyclohexene Oxide and Derivatives Using a Mono(μ-Alkoxo)bis(alkylaluminum) Initiator

Pedretti, Benjamin J.; Zhu, Congzhi; Watanabe, Hironobu; Aoshima, Sadahito; Lynd, Nathaniel A.

doi:10.1021/acs.macromol.3c00473

Cascade Ring Strain Release Polymerization of Cyclohexene Oxide and Derivatives Using a Mono(μ-Alkoxo)bis(alkylaluminum) Initiator

Journal Article · 30 June 2023 · Macromolecules

DOI:https://doi.org/10.1021/acs.macromol.3c00473· OSTI ID:2421076

^[1]; ^[2]; ^[3]; ^[3]; ^[4]

McKetta Department of Chemical Engineering, The University of Texas at Austin, Austin, Texas 78712, United States; OSTI
McKetta Department of Chemical Engineering, The University of Texas at Austin, Austin, Texas 78712, United States
Department of Macromolecular Science, Graduate School of Science, Osaka University, Toyonaka, Osaka 560-0043, Japan
McKetta Department of Chemical Engineering, The University of Texas at Austin, Austin, Texas 78712, United States; Texas Materials Institute, The University of Texas at Austin, Austin, Texas 78712, United States

Not provided.

Research Organization:: Univ. of Texas, Austin, TX (United States)

Sponsoring Organization:: USDOE Office of Science (SC)

DOE Contract Number:: SC0019272

OSTI ID:: 2421076

Journal Information:: Macromolecules, Journal Name: Macromolecules Journal Issue: 13 Vol. 56; ISSN 0024-9297

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

References (83)

Catalytic Phosphorus(V)-Mediated Nucleophilic Substitution Reactions: Development of a Catalytic Appel Reaction Denton, Ross M.; An, Jie; Adeniran, Beatrice The Journal of Organic Chemistry, Vol. 76, Issue 16 https://doi.org/10.1021/jo201085r	journal	July 2011
Ring-Opening Polymerization of Epoxides: Facile Pathway to Functional Polyethers via a Versatile Organoaluminum Initiator Rodriguez, Christina G.; Ferrier, Robert C.; Helenic, Alysha Macromolecules, Vol. 50, Issue 8 https://doi.org/10.1021/acs.macromol.7b00196	journal	April 2017
Organometallic catalysts for polymerizing monosubstituted epoxides Vandenberg, E. J. Journal of Polymer Science, Vol. 47, Issue 149 https://doi.org/10.1002/pol.1960.1204714947	journal	November 1960
Role of Backbone Chemistry and Monomer Sequence in Amphiphilic Oligopeptide- and Oligopeptoid-Functionalized PDMS- and PEO-Based Block Copolymers for Marine Antifouling and Fouling Release Coatings Patterson, Anastasia L.; Wenning, Brandon; Rizis, Georgios Macromolecules, Vol. 50, Issue 7 https://doi.org/10.1021/acs.macromol.6b02505	journal	March 2017
Triblock copolymers from lactide and telechelic poly(cyclohexene carbonate) Kember, Michael R.; Copley, James; Buchard, Antoine Polymer Chemistry, Vol. 3, Issue 5 https://doi.org/10.1039/C2PY00543C	journal	January 2012
Synthesis of functional and architectural polyethers via the anionic ring-opening polymerization of epoxide monomers using a phosphazene base catalyst Isono, Takuya Polymer Journal, Vol. 53, Issue 7 https://doi.org/10.1038/s41428-021-00481-3	journal	April 2021
Synthesis and characterization of segmented polyurethanes based on amphiphilic polyether diols Lan, P. Biomaterials, Vol. 17, Issue 23 https://doi.org/10.1016/0142-9612(96)00056-7	journal	January 1996
Polymerization of Ethylene Oxide, Propylene Oxide, and Other Alkylene Oxides: Synthesis, Novel Polymer Architectures, and Bioconjugation Herzberger, Jana; Niederer, Kerstin; Pohlit, Hannah Chemical Reviews, Vol. 116, Issue 4 https://doi.org/10.1021/acs.chemrev.5b00441	journal	December 2015
Mechanistic Studies of Redox-Switchable Copolymerization of Lactide and Cyclohexene Oxide by a Zirconium Complex Quan, Stephanie M.; Wei, Junnian; Diaconescu, Paula L. Organometallics, Vol. 36, Issue 22 https://doi.org/10.1021/acs.organomet.7b00672	journal	November 2017
Experimental and Computational Investigation of the Mechanism of Carbon Dioxide/Cyclohexene Oxide Copolymerization Using a Dizinc Catalyst Buchard, Antoine; Jutz, Fabian; Kember, Michael R. Macromolecules, Vol. 45, Issue 17 https://doi.org/10.1021/ma300803b	journal	August 2012
Vinyl Epoxides in Organic Synthesis He, Jiayun; Ling, Jesse; Chiu, Pauline Chemical Reviews, Vol. 114, Issue 16 https://doi.org/10.1021/cr400709j	journal	April 2014
Chemoselective Polymerizations from Mixtures of Epoxide, Lactone, Anhydride, and Carbon Dioxide Romain, Charles; Zhu, Yunqing; Dingwall, Paul Journal of the American Chemical Society, Vol. 138, Issue 12 https://doi.org/10.1021/jacs.5b13070	journal	March 2016
ABC and ABAB Block Copolymers by Electrochemically Controlled Ring-Opening Polymerization Hern, Zachary C.; Quan, Stephanie M.; Dai, Ruxi Journal of the American Chemical Society, Vol. 143, Issue 47 https://doi.org/10.1021/jacs.1c08648	journal	November 2021
Alternating Copolymerization of Propylene Oxide and Cyclohexene Oxide with Tricyclic Anhydrides: Access to Partially Renewable Aliphatic Polyesters with High Glass Transition Temperatures Sanford, Maria J.; Peña Carrodeguas, Leticia; Van Zee, Nathan J. Macromolecules, Vol. 49, Issue 17 https://doi.org/10.1021/acs.macromol.6b01425	journal	August 2016
Stereospecific polymerization of cyclohexene oxide Sepulchre, M.; Kassamaly, A.; Spassky, N. Makromolekulare Chemie. Macromolecular Symposia, Vol. 42-43, Issue 1 https://doi.org/10.1002/masy.19910420140	journal	March 1991
Visible Light Induced Cationic Polymerization of Epoxides by Using Multiwalled Carbon Nanotubes Sangermano, Marco; Rodriguez, Damian; Gonzalez, Monica C. Macromolecular Rapid Communications, Vol. 39, Issue 13 https://doi.org/10.1002/marc.201800250	journal	May 2018
Epicyanohydrin: Polymerization by Monomer Activation Gives Access to Nitrile-, Amino-, and Carboxyl-Functional Poly(ethylene glycol) Herzberger, Jana; Frey, Holger Macromolecules, Vol. 48, Issue 22 https://doi.org/10.1021/acs.macromol.5b02178	journal	October 2015
Enantioselective Polymerization of Epoxides: A Highly Active and Selective Catalyst for the Preparation of Stereoregular Polyethers and Enantiopure Epoxides Hirahata, Wataru; Thomas, Renee M.; Lobkovsky, Emil B. Journal of the American Chemical Society, Vol. 130, Issue 52 https://doi.org/10.1021/ja807709j	journal	December 2008
Copolymerization of cyclohexene oxide and carbon dioxide using (salen)Co(iii) complexes: synthesis and characterization of syndiotactic poly(cyclohexene carbonate) Cohen, Claire T.; Thomas, Christophe M.; Peretti, Kathryn L. Dalton Trans., Issue 1 https://doi.org/10.1039/B513107C	journal	January 2006
Chemical Recycling of Poly(Cyclohexene Carbonate) Using a Di‐Mg^II Catalyst Singer, Frances N.; Deacy, Arron C.; McGuire, Thomas M. Angewandte Chemie International Edition, Vol. 61, Issue 26 https://doi.org/10.1002/anie.202201785	journal	May 2022
Di- and Tri-Zinc Catalysts for the Low-Pressure Copolymerization of CO₂ and Cyclohexene Oxide Kember, Michael R.; White, Andrew J. P.; Williams, Charlotte K. Inorganic Chemistry, Vol. 48, Issue 19 https://doi.org/10.1021/ic901109e	journal	August 2009
Controllable Synthesis of Stereoregular Polyesters by Organocatalytic Alternating Copolymerizations of Cyclohexene Oxide and Norbornene Anhydrides Han, Bing; Zhang, Li; Liu, Binyuan Macromolecules, Vol. 48, Issue 11 https://doi.org/10.1021/acs.macromol.5b00555	journal	May 2015
Epoxide polymers: Synthesis, stereochemistry, structure, and mechanism Vandenberg, E. J. Journal of Polymer Science Part A-1: Polymer Chemistry, Vol. 7, Issue 2 https://doi.org/10.1002/pol.1969.150070210	journal	February 1969
Properties of polyether-polyurethane block copolymers: effects of hard segment length distribution Miller, John A.; Lin, Shaow B.; Hwang, Kirk K. S. Macromolecules, Vol. 18, Issue 1 https://doi.org/10.1021/ma00143a005	journal	January 1985
Chromium Amino-bis(phenolate) Complexes as Catalysts for Ring-Opening Polymerization of Cyclohexene Oxide Ambrose, Kenson; Murphy, Jennifer N.; Kozak, Christopher M. Macromolecules, Vol. 52, Issue 19 https://doi.org/10.1021/acs.macromol.9b01381	journal	September 2019
Studies on elementary reactions in the polymerization of 1,2‐epoxycyclohexane with organozinc compounds as initiators Hasebe, Yoshihiro; Izumitani, Keiko; Torii, Masao Die Makromolekulare Chemie, Vol. 191, Issue 1 https://doi.org/10.1002/macp.1990.021910109	journal	January 1990
Heterotrinuclear Ring Opening Copolymerization Catalysis: Structure–activity Relationships Plajer, Alex J.; Williams, Charlotte K. ACS Catalysis, Vol. 11, Issue 24 https://doi.org/10.1021/acscatal.1c04449	journal	November 2021
Stereoselective Ring-Opening Polymerization of Lactones with a Fused Ring Leading to Semicrystalline Polyesters Yang, Xing; Zhang, Wei; Huang, Hao-Yi Macromolecules, Vol. 55, Issue 7 https://doi.org/10.1021/acs.macromol.1c02555	journal	March 2022
Electrochemically Switchable Ring-Opening Polymerization of Lactide and Cyclohexene Oxide Qi, Miao; Dong, Qi; Wang, Dunwei Journal of the American Chemical Society, Vol. 140, Issue 17 https://doi.org/10.1021/jacs.8b02171	journal	April 2018
Four-fold increase in epoxide polymerization rate with change of alkyl-substitution on mono-μ-oxo-dialuminum initiators Ferrier, R. C.; Imbrogno, J.; Rodriguez, C. G. Polymer Chemistry, Vol. 8, Issue 31 https://doi.org/10.1039/C7PY00894E	journal	January 2017
Epihalohydrins in Organic Synthesis Singh, Girija S.; Mollet, Karen; D’hooghe, Matthias Chemical Reviews, Vol. 113, Issue 3 https://doi.org/10.1021/cr3003455	journal	December 2012
Decoupling Catalysis and Chain-Growth Functions of Mono(μ-alkoxo)bis(alkylaluminums) in Epoxide Polymerization: Emergence of the N–Al Adduct Catalyst Imbrogno, Jennifer; Ferrier, Robert C.; Wheatle, Bill K. ACS Catalysis, Vol. 8, Issue 9 https://doi.org/10.1021/acscatal.8b02446	journal	August 2018
Poly(allyl glycidyl ether)-A versatile and functional polyether platform Lee, Bongjae F.; Kade, Matthew J.; Chute, Jerred A. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 49, Issue 20 https://doi.org/10.1002/pola.24891	journal	August 2011
Polyether synthesis: From activated or metal-free anionic ring-opening polymerization of epoxides to functionalization Brocas, Anne-Laure; Mantzaridis, Christos; Tunc, Deniz Progress in Polymer Science, Vol. 38, Issue 6 https://doi.org/10.1016/j.progpolymsci.2012.09.007	journal	June 2013
Investigation of the Reactivity of Epoxide Monomers in Photoinitiated Cationic Polymerization Bulut, Umut; Crivello, James V. Macromolecules, Vol. 38, Issue 9 https://doi.org/10.1021/ma050106k	journal	April 2005
Metal Salt-Promoted Alcoholysis of 1,2-Epoxides Chini, Marco; Crotti, Paolo; Gardelli, Cristina Synlett, Vol. 1992, Issue 08 https://doi.org/10.1055/s-1992-21454	journal	January 1992
Regiochemical control of the ring-opening of 1,2-epoxides by means of chelating processes. Synthesis and reactions of the cis- and trans-oxides derived from 4-(benzyloxy)cyclohexene Chini, Marco; Crotti, Paolo; Flippin, Lee A. The Journal of Organic Chemistry, Vol. 55, Issue 14 https://doi.org/10.1021/jo00301a011	journal	July 1990
In situ reactions with trichloroacetyl isocyanate and their application to structural assignment of hydroxy compounds by 1H NMR spectroscopy. A general comment Samek, Zdeněk; Buděšínský, Miloš Collection of Czechoslovak Chemical Communications, Vol. 44, Issue 2 https://doi.org/10.1135/cccc19790558	journal	January 1979
Highly Active Di- and Trimetallic Cobalt Catalysts for the Copolymerization of CHO and CO₂ at Atmospheric Pressure Kember, Michael R.; White, Andrew J. P.; Williams, Charlotte K. Macromolecules, Vol. 43, Issue 5 https://doi.org/10.1021/ma902582m	journal	February 2010
Über Steroide und Sexualhormone. 160. Mitteilung. 2α, 3α‐ und 2β, 3β‐Oxido‐chlolestane; Konfiguration der 2‐Oxy‐cholestane Fürst, A.; Plattner, Pl. A. Helvetica Chimica Acta, Vol. 32, Issue 1 https://doi.org/10.1002/hlca.19490320139	journal	February 1949
Exploration of Cocatalyst Effects on a Bimetallic Cobalt Catalyst System: Enhanced Activity and Enantioselectivity in Epoxide Polymerization Widger, Peter C. B.; Ahmed, Syud M.; Coates, Geoffrey W. Macromolecules, Vol. 44, Issue 14 https://doi.org/10.1021/ma201078m	journal	July 2011
Poly(ethylene glycol- co -allyl glycidyl ether)s: A PEG-Based Modular Synthetic Platform for Multiple Bioconjugation Obermeier, Boris; Frey, Holger Bioconjugate Chemistry, Vol. 22, Issue 3 https://doi.org/10.1021/bc1004747	journal	March 2011
High polymers from symmetrical disubstituted epoxides Vandenberg, E. J. Journal of Polymer Science, Vol. 47, Issue 149 https://doi.org/10.1002/pol.1960.1204714948	journal	November 1960
Catalysts for CO ₂ /epoxide ring-opening copolymerization Trott, G.; Saini, P. K.; Williams, C. K. Philosophical Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences, Vol. 374, Issue 2061 https://doi.org/10.1098/rsta.2015.0085	journal	February 2016
Chemical recycling to monomer for an ideal, circular polymer economy Coates, Geoffrey W.; Getzler, Yutan D. Y. L. Nature Reviews Materials, Vol. 5, Issue 7 https://doi.org/10.1038/s41578-020-0190-4	journal	April 2020
Allyl Glycidyl Ether-Based Polymer Electrolytes for Room Temperature Lithium Batteries Barteau, Katherine P.; Wolffs, Martin; Lynd, Nathaniel A. Macromolecules, Vol. 46, Issue 22 https://doi.org/10.1021/ma401267w	journal	November 2013
Synthetically Useful Reactions of Epoxides Gorzynski Smith, Janice Synthesis, Vol. 1984, Issue 08 https://doi.org/10.1055/s-1984-30921	journal	January 1984
Exploiting Sodium Coordination in Alternating Monomer Sequences to Toughen Degradable Block Polyester Thermoplastic Elastomers Gregory, Georgina L.; Williams, Charlotte K. Macromolecules, Vol. 55, Issue 6 https://doi.org/10.1021/acs.macromol.2c00068	journal	March 2022
Stereoselective Epoxide Polymerization and Copolymerization Childers, M. Ian; Longo, Julie M.; Van Zee, Nathan J. Chemical Reviews, Vol. 114, Issue 16 https://doi.org/10.1021/cr400725x	journal	July 2014
Living Cationic Ring-Opening Homo- and Copolymerization of Cyclohexene Oxide by “Dormant” Species Generation Using Cyclic Ethers as Lewis Basic Additives Inoue, Masamichi; Kanazawa, Arihiro; Aoshima, Sadahito Macromolecules, Vol. 54, Issue 11 https://doi.org/10.1021/acs.macromol.1c00654	journal	May 2021
Mechanistic Investigation and Reaction Kinetics of the Low-Pressure Copolymerization of Cyclohexene Oxide and Carbon Dioxide Catalyzed by a Dizinc Complex Jutz, Fabian; Buchard, Antoine; Kember, Michael R. Journal of the American Chemical Society, Vol. 133, Issue 43 https://doi.org/10.1021/ja206352x	journal	November 2011
Redox Switchable Copolymerization of Cyclic Esters and Epoxides by a Zirconium Complex Quan, Stephanie M.; Wang, Xinke; Zhang, Rongjia Macromolecules, Vol. 49, Issue 18 https://doi.org/10.1021/acs.macromol.6b00997	journal	September 2016
Bimetallic Cobalt Complex-Mediated Enantioselective Terpolymerizations of Carbon Dioxide, Cyclohexene Oxide, and β-Butyrolactone Li, Wen-Bing; Liu, Ye; Lu, Xiao-Bing Organometallics, Vol. 39, Issue 9 https://doi.org/10.1021/acs.organomet.9b00782	journal	January 2020
Chemical Upcycling of Poly(3-hydroxybutyrate) into Bicyclic Ether–Ester Monomers toward Value-Added, Degradable, and Recyclable Poly(ether ester) Li, Zheng; Shen, Yong; Li, Zhibo ACS Sustainable Chemistry & Engineering, Vol. 10, Issue 25 https://doi.org/10.1021/acssuschemeng.2c02124	journal	June 2022
Crystal Structures and Glassy Phase Transition Behavior of Cyclohexene Ibberson, Richard M.; Telling, Mark T. F.; Parsons, Simon Crystal Growth & Design, Vol. 8, Issue 2 https://doi.org/10.1021/cg0705512	journal	December 2007
Ring-opening polymerization of cyclohexene oxide using aluminum amine–phenolate complexes Plommer, Hart; Reim, Immanuel; Kerton, Francesca M. Dalton Transactions, Vol. 44, Issue 27 https://doi.org/10.1039/C5DT00220F	journal	January 2015
Facial Selectivity in Epoxidation of 2-Cyclohexen-1-ol with Peroxy Acids. A Computational DFT Study Freccero, Mauro; Gandolfi, Remo; Sarzi-Amadè, Mirko The Journal of Organic Chemistry, Vol. 65, Issue 26 https://doi.org/10.1021/jo000900y	journal	November 2000
The versatile, functional polyether, polyepichlorohydrin: History, synthesis, and applications Shukla, Geetanjali; Ferrier, Robert C. Journal of Polymer Science, Vol. 59, Issue 22 https://doi.org/10.1002/pol.20210514	journal	October 2021
Controlled High-Speed Anionic Polymerization of Propylene Oxide Initiated by Onium Salts in the Presence of Triisobutylaluminum Labbé, Amélie; Carlotti, Stéphane; Billouard, Cyrille Macromolecules, Vol. 40, Issue 22 https://doi.org/10.1021/ma070288d	journal	October 2007
Structural studies of poly(1,2‐cyclohexene oxide) prepared with well‐defined organozinc compounds Hasebe, Yoshihiro; Tsuruta, Teiji Die Makromolekulare Chemie, Vol. 188, Issue 6 https://doi.org/10.1002/macp.1987.021880616	journal	June 1987
Heterodinuclear Mg(II)M(II) (M=Cr, Mn, Fe, Co, Ni, Cu and Zn) Complexes for the Ring Opening Copolymerization of Carbon Dioxide/Epoxide and Anhydride/Epoxide Reis, Natalia V.; Deacy, Arron C.; Rosetto, Gloria Chemistry – A European Journal, Vol. 28, Issue 14 https://doi.org/10.1002/chem.202104198	journal	February 2022
Regiochemical control of the ring-opening of 1,2-epoxides by means of chelating processes. 2. Synthesis and reactions of the cis- and trans-oxides of 4-[(benzyloxy)methyl]cyclohexene, 3-cyclohexenemethanol, and methyl 3-cyclohexenecarboxylate Chini, Marco; Crotti, Paolo; Flippin, Lee A. The Journal of Organic Chemistry, Vol. 57, Issue 5 https://doi.org/10.1021/jo00031a018	journal	February 1992
Block Copolymerization of Lactide and an Epoxide Facilitated by a Redox Switchable Iron-Based Catalyst Biernesser, Ashley B.; Delle Chiaie, Kayla R.; Curley, Julia B. Angewandte Chemie International Edition, Vol. 55, Issue 17 https://doi.org/10.1002/anie.201511793	journal	March 2016
Aliphatic Polyester Block Polymer Design Schneiderman, Deborah K.; Hillmyer, Marc A. Macromolecules, Vol. 49, Issue 7 https://doi.org/10.1021/acs.macromol.6b00211	journal	March 2016
Molecular diffusion in polymeric systems Duda, J. L. Pure and Applied Chemistry, Vol. 57, Issue 11 https://doi.org/10.1351/pac198557111681	journal	January 1985
Some aspects of the bimetallic μ‐oxo‐alkoxides for polymerizing epoxides to polyether elastomers Vandenberg, E. J. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 24, Issue 7 https://doi.org/10.1002/pola.1986.080240701	journal	July 1986
Mechanisms Of Epoxide Reactions Parker, R. E.; Isaacs, N. S. Chemical Reviews, Vol. 59, Issue 4 https://doi.org/10.1021/cr50028a006	journal	August 1959
Alternating Ring-Opening Polymerization of Cyclohexene Oxide and Anhydrides: Effect of Catalyst, Cocatalyst, and Anhydride Structure Hosseini Nejad, Elham; van Melis, Carlo G. W.; Vermeer, Tim J. Macromolecules, Vol. 45, Issue 4 https://doi.org/10.1021/ma2025804	journal	February 2012
Hyperbranched polyethers with tunable glass transition temperature: controlled synthesis and mixing rules Liu, Tuan; Geng, Xinxin; Nie, Yongxing RSC Adv., Vol. 4, Issue 57 https://doi.org/10.1039/C4RA04077E	journal	January 2014
How Lewis Acids Catalyze Ring-Openings of Cyclohexene Oxide Hansen, Thomas; Vermeeren, Pascal; Yoshisada, Ryoji The Journal of Organic Chemistry, Vol. 86, Issue 4 https://doi.org/10.1021/acs.joc.0c02955	journal	February 2021
Asymmetric Alternating Copolymerization of Cyclohexene Oxide and CO ₂ with Dimeric Zinc Complexes Nakano, Koji; Nozaki, Kyoko; Hiyama, Tamejiro Journal of the American Chemical Society, Vol. 125, Issue 18 https://doi.org/10.1021/ja028666b	journal	May 2003
Synthesis and physical characterization of poly(cyclohexane carbonate), synthesized from CO2 and cyclohexene oxide Koning, C.; Wildeson, J.; Parton, R. Polymer, Vol. 42, Issue 9 https://doi.org/10.1016/S0032-3861(00)00709-6	journal	April 2001
Effects of Poly(glycidyl ether) Structure and Ether Oxygen Placement on CO₂ Solubility Bentley, Caitlin L.; Song, Tangqiumei; Pedretti, Benjamin J. Journal of Chemical & Engineering Data, Vol. 66, Issue 7 https://doi.org/10.1021/acs.jced.1c00219	journal	June 2021
Di-magnesium and zinc catalysts for the copolymerization of phthalic anhydride and cyclohexene oxide Saini, Prabhjot K.; Romain, Charles; Zhu, Yunqing Polym. Chem., Vol. 5, Issue 20 https://doi.org/10.1039/C4PY00748D	journal	January 2014
Comparison between properties of polyether polytriazole elastomers and polyether polyurethane elastomers Qu, Zhengyang; Zhai, Jinxian; Yang, Rongjie Polymers for Advanced Technologies, Vol. 25, Issue 3 https://doi.org/10.1002/pat.3242	journal	January 2014
Rigid Hyperbranched Polycarbonate Polyols from CO₂ and Cyclohexene-Based Epoxides Scharfenberg, Markus; Hofmann, Silja; Preis, Jasmin Macromolecules, Vol. 50, Issue 16 https://doi.org/10.1021/acs.macromol.7b01276	journal	August 2017
A new visible light sensitive photoinitiator system for the cationic polymerization of epoxides Crivello, James V. Journal of Polymer Science Part A: Polymer Chemistry, Vol. 47, Issue 3 https://doi.org/10.1002/pola.23203	journal	December 2008
Regiochemical control of the ring-opening of 1,2-epoxides by means of chelating processes. 3. Aminolysis and azidolysis of the cis- and trans-oxides derived from 4-(benzyloxy)cyclohexene Chini, Marco; Crotti, Paolo; Flippin, Lee A. The Journal of Organic Chemistry, Vol. 56, Issue 25 https://doi.org/10.1021/jo00025a018	journal	December 1991
Redox-Switchable Ring-Opening Polymerization with Ferrocene Derivatives Wei, Junnian; Diaconescu, Paula L. Accounts of Chemical Research, Vol. 52, Issue 2 https://doi.org/10.1021/acs.accounts.8b00523	journal	January 2019
Investigation of a zirconium compound for redox switchable ring opening polymerization Dai, Ruxi; Diaconescu, Paula L. Dalton Transactions, Vol. 48, Issue 9 https://doi.org/10.1039/C9DT00212J	journal	January 2019
Preparation and performance of polyether elastomer with a combination of polyurethane and polytriazole Cong, Kun; Liu, Zhenhui; He, Jiyu Journal of Applied Polymer Science, Vol. 139, Issue 12 https://doi.org/10.1002/app.51842	journal	November 2021
Stereo- and regioselective metal salt-catalyzed alkynylation of 1,2-epoxides Chini, Marco; Crotti, Paolo; Favero, Lucilla Tetrahedron Letters, Vol. 32, Issue 45 https://doi.org/10.1016/0040-4039(91)80237-Z	journal	November 1991
Advancing the Development of Recyclable Aromatic Polyesters by Functionalization and Stereocomplexation Fan, Hua‐Zhong; Yang, Xing; Chen, Jia‐Hao Angewandte Chemie, Vol. 134, Issue 15 https://doi.org/10.1002/ange.202117639	journal	February 2022

Similar Records

User Guide to Ring-Opening Metathesis Polymerization of endo -Norbornene Monomers with Chelated Initiators

Journal Article · 2022 · Macromolecules · OSTI ID:1978165

Synchrotron Photoionization Measurements of OH-initiated Cyclohexene Oxidation: Absence of Ring-Opening Products in OH %2B Cyclohexene and Hydroxycyclohexyl %2B O2 Reactions.

Journal Article · 2012 · Proposed for publication in Journal of Physical Chemistry A. · OSTI ID:1068442

RADIATION-INDUCED POLYMERIZATION OF 1,2-CYCLOHEXENE OXIDE

Journal Article · 1965 · J. Polymer Sci. Pt. A · OSTI ID:4596131

Related Subjects

Polymer Science

Cascade Ring Strain Release Polymerization of Cyclohexene Oxide and Derivatives Using a Mono(μ-Alkoxo)bis(alkylaluminum) Initiator

Citation Formats

References (83)

Similar Records

Related Subjects