2646-84-6Relevant articles and documents
Synthesis and aromatization of 2+2 cycloadducts of butadienes and tetrafluoroethylene
Weigert, F. J.,Davis, R. F.
, p. 69 - 84 (1993)
Passing tetrafluoroethylene (TFE) and hydrocarbon dienes down a hot tube at 600 deg C with a contact time of a few seconds produces substituted fluorobenzenes.Specifically, tetrafluoroethylene and butadiene form 1,2-difluorobenzene.The aromatics produced bythe pyrolysis of TFE and methyl-substituted butadienes do not necessarily result from eliminating HF from 2+4 adducts of the starting materials.Solid-acids such as alumina or silica/alumina accelerate the ring-expansion elimination of the 2+2 cycloadducts.Aromatic products result from the preformed 2+2 cycloadducts at temperatures 200 deg C lower than the corresponding thermal reaction.The solid-acids can also influence product regiochemistry.
Three-step regioselective synthesis of 2,3-difluorohalobenzenes using tetrafluoroethylene and buta-1,3-diene as starting building blocks
Egorov, M. P.,Lipkind, M. B.,Nefedov, O. M.,Volchkov, N. V.
, p. 925 - 932 (2021/06/07)
The gas-phase copyrolysis of tetrafluoroethylene and buta-1,3-diene in a flow tube reactor at 490–510 °C gives 3,3,4,4-tetrafluorocyclohex-1-ene, which is selectively converted to 1-bromo- or 1-chloro-2,3-difluorobenzene via intermediate steps of halogenation and dehydrohalogenation.
Synthesis of fluorinated halonitrobenzenes and halonitrophenols using tetrafluoroethylene and buta-1,3-dienes as starting building blocks
Lipkind, M. B.,Nefedov, O. M.,Volchkov, N. V.
, p. 2156 - 2163 (2022/01/22)
The gas-phase copyrolysis of tetrafluoroethylene with buta-1,3-diene in a flow reactor at 495–505 °C produces 3,3,4,4-tetrafluorocyclohex-1-ene, which selectively converted to 1,2-difluorobenzene or 1-chloro-2,3-difluorobenzene. The latter can be converted to 2-chloro-3,4-difluoronitrobenzene, 2,3,4-trifluoronitrobenzene, 2,3-difluoro-6-nitrophenol, or 2-chloro-3-fluoro-4-nitrophenol via nitration, fluorodechlorination, and hydrolysis reactions.
KINETICS AND MECHANISM OF THE SYNTHESIS OF DIFLUOROBENZENES BY THERMAL REACTION OF DIFLUOROCARBENE WITH BUTADIENE
Shipilov, A. I.,Zabolot-skikh, V. F.,Nefedov, O. M.
, p. 77 - 85 (2007/10/02)
Reaction of butadiene with difluorocarbene, resulting in the formation of difluorobenzenes, and its main steps have been systematically studied.The kinetics of thermal conversions of intermediately formed 2,2-difluorovinylcyclopropane and 2,2,3,3-tetrafluorovinylcyclobutane has been examined.The synthesis of difluorobenzenes has been optimized.The results obtained are used as a basis for domestic technology of production of difluorobenzenes.
