24.2. 1.3 1,1-Dihaloalk-1-enes (Update 2014)
Book
Editors: Banert, K.; Brøndsted Nielsen, M.; Drabowicz, J.; Joule, J. A.; Schaumann, E.; Weinreb, S. M.
Title: Knowledge Updates 2014/3
Print ISBN: 9783131762818; Online ISBN: 9783131975119; Book DOI: 10.1055/b-003-125830
1st edition © 2014 Thieme. All rights reserved.
Georg Thieme Verlag KG, Stuttgart
Subjects: Organic Chemistry;Chemical Reactions, Catalysis;Organometallic Chemistry;Laboratory Techniques, Stoichiometry
Science of Synthesis Knowledge Updates
Parent publication
Title: Science of Synthesis
DOI: 10.1055/b-00000101
Series Editors: Carreira, E. M.; Decicco, C. P.; Fürstner, A.; Molander, G. A.; Schaumann, E.; Shibasaki, M.; Thomas, E. J.; Trost, B. M.
Type: Multivolume Edition
Abstract

This chapter is an update to the earlier Science of Synthesis contribution describing methods and strategies for the synthesis of 1,1-dihaloalk-1-enes. This update focuses on the preparation and polymerization of 1,1-difluoroalk-1-enes, including trifluorovinyl functional monomers. Radical additions of chain-transfer agents onto commercially available fluoroalkenes are described, followed by their chemical modification to yield original fluorinated monomers. These monomers are further involved in radical (conventional or controlled) copolymerizations with vinylidene fluoride (1,1-difluoroethene) or chlorotrifluoroethene to achieve high-value-added materials.
Key words
1,1-dihaloalk-1-enes - chlorotrifluoroethene - fluoropolymers - fuel-cell membranes - NMR - radical copolymerization - trifluorovinyl functional monomers - vinylidene fluoride - 1,1-difluoroethene- 4 Fluoropolymers 2: Properties. Hougham G, Cassidy PE, Johns K, Davidson T. Kluwer/Plenum; New York 1999
- 6 Ameduri B, Boutevin B. Well-Architectured Fluoropolymers: Synthesis, Properties and Applications. Elsevier; Amsterdam 2004
- 8 Feiring AE, In: Organofluorine Chemistry: Principles and Commercial Applications Banks RE, Smart BE, Tatlow JC. Plenum New York 1994; 15. 339-372
-
12 Puts G, Ameduri B, Crouse P, In: Handbook of Fluoropolymer Science and Technology Smith DW, Iyer SS, Iacono ST. Wiley New York 2014; 5
- 17 German LS, Grigor’ev LS, Kolbanovskii YuA, Chepik SD. Izv. Akad. Nauk SSSR, Ser. Khim. 1987; 2143 Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 1987; 36,: 1994
-
19 Dohany JE, In: Kirk-Othmer Encyclopedia of Chemical Technology Kirk RE, Othmer D. Wiley New York 1998;
- 20 Humphrey JS, Amin-Sanayei R, In: Encyclopedia of Polymer Science and Technology Mark HF. Wiley New York 2004; 4. 510
-
21 Accessed .2 14, 13.0 at: http://www.inchem.org/documents/sids/sids/VDFF2.pdf
- 55 Kremlev MM, Cherednichenko PG, Moklyachuk LI, Yagupol’skii LM. Zh. Org. Khim. 1989; 25: 2582 J. Org. Chem. USSR (Engl. Transl.) 1989; 25: 2316
- 56 Kremlev MM, Moklyachuk LI, Fialkov YuA, Yagupol’skii LM. Zh. Org. Khim. 1984; 20: 1162 J. Org. Chem. USSR (Engl. Transl.) 1984; 20: 1057
- 61 Kostov G, Ameduri B, Boutevin B, Bauduin G, Stankova M. J. Polym. Sci., Part A: Polym. Chem. 2004; 42: 1693
- 73 Guiot J, Neouze MA, Sauguet L, Ameduri B, Boutevin B. J. Polym. Sci., Part A: Polym. Chem. 2005; 43: 917
- 75 Thenappan A, Rainal E, Ameduri B, Boschet F, Ajellal N, Lopez G. US 2 013 184 422, 2013 Chem. Abstr.. 2013 159 213 664
-
96 Dolbier Jr WR, Rong XX, Bartberger MD, Koroniak H, Smart BE, Yang Z.-Y. J. Chem. Soc., Perkin Trans. 2 1998; 219
- 117 Sel O, Soules A, Ameduri B, Boutevin B, Laberty-Robert C, Gebel G, Sanchez C. Adv. Funct. Mater. 2010; 20: 1090
- 123 Oka M, Tatemoto M, In: Contemporary Topics in Polymer Science Bailey WJ, Tsuruta T. Plenum New York 1984; 4. 763-778
-
124 Tatemoto M, In: Polymeric Materials Encyclopedia Salamone JC. CRC Boca Raton, FL, (1996); Vol. 5, pp 3847-3862