Thermal and BF3?Et2O-catalyzed cleavage of 1-hydrohexafluoroisobutenyloxytrimethylsilane. Perfluoromethacrolein, its isomers, dimers, and homopolymers

Autor:	E. M. Kagramanova, N. E. Mysova, E. I. Mysov, A. Yu. Volkonskii
Rok vydání:	2004
Předmět:	chemistry.chemical_compound Trifluoromethyl chemistry Thermal Cleavage (crystal) General Chemistry Photochemistry Silane Pyrolysis Quartz Fluoride Catalysis
Zdroj:	Russian Chemical Bulletin. 53:1693-1699
ISSN:	1573-9171 1066-5285
DOI:	10.1007/s11172-005-0019-8
Popis:	During vacuum pyrolysis in a quartz or steel tube, 1-hydrohexafluoroisobutenyloxytrimethylsilane (1) eliminates fluorotrimethylsilane to give perfluoromethacrolein, which was detected by NMR. Similar pyrolysis of silane 1 over KF results in E- and Z-β-hydrotetrafluoromethacryloyl fluorides. At 20 °C, perfluoromethacrolein undergoes homopolymerisation and/or cyclodimerization to yield 4,4-difluoro-2-pentafluoroisopropenyl-5-trifluoromethyl-4H-1,3-dioxin, which rearranges into E-7,7,7-trifluoro-2,6-bis(trifluoromethyl)-4-oxahepta-2,5-dienoyl fluoride under the action of BF3⋅Et2O. The same fluoride is also formed, together with fluorotrimethylsilane, directly from silane 1 under the action of BF3⋅Et2O.
Databáze:	OpenAIRE
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