Synthesis of fluorinated halonitrobenzenes and halonitrophenols using tetrafluoroethylene and buta-1,3-dienes as starting building blocks

被引:1
作者
Volchkov, N. V. [1 ]
Lipkind, M. B. [1 ]
Nefedov, O. M. [1 ]
机构
[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia
关键词
tetrafluoroethylene; buta-1; 3-diene; cycloaddition; tetrafluorocyclohexenes; halogenation; dehydrohalogenation; 1; 2-difluorobenzene; 1-chloro-2; 3-difluorobenzene; nitration; chlorodifluoronitrobenzenes; 3; 4-difluoronitrobenzenes; 2; 4-trifluoronitrobenzene; 3-difluoro-6-nitrophenol; chlorofluoronitrophenols; AROMATIC FLUORIDES; ANTIBACTERIAL ACTIVITIES; REGIOSELECTIVE SYNTHESIS; 2+2 CYCLOADDUCTS; DERIVATIVES; CATALYSTS; CYCLOPENTADIENE; HYDROGENATION; BUTADIENES; AMINES;
D O I
10.1007/s11172-021-3327-8
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The gas-phase copyrolysis of tetrafluoroethylene with buta-1,3-diene in a flow reactor at 495-505 degrees 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.
引用
收藏
页码:2156 / 2163
页数:8
相关论文
共 55 条
[1]  
Andriole V.T., 1998, QUINOLONES, Vsecond
[2]  
ATARASHI S, 1987, CHEM PHARM BULL, V35, P1896
[3]   Organic fluorine compounds: a great opportunity for enhanced materials properties [J].
Berger, Ricarda ;
Resnati, Giuseppe ;
Metrangolo, Pierangelo ;
Weber, Edwin ;
Hulliger, Juerg .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (07) :3496-3508
[4]   NUCLEOPHILIC DISPLACEMENT IN POLY-HALOGENO-AROMATIC COMPOUNDS .7. KINETICS OF METHOXY-DEFLUORINATION OF POLYFLUORONITROBENZENES [J].
BOLTON, R ;
SANDALL, JPB .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1978, (02) :141-144
[5]   Modern Carbon-Fluorine Bond Forming Reactions for Aryl Fluoride Synthesis [J].
Campbell, Michael G. ;
Ritter, Tobias .
CHEMICAL REVIEWS, 2015, 115 (02) :612-633
[6]   Elemental fluorine Part 12. Fluorination of 1,4-disubstituted aromatic compounds [J].
Chambers, RD ;
Hutchinson, J ;
Sparrowhawk, ME ;
Sandford, G ;
Moilliet, JS ;
Thomson, J .
JOURNAL OF FLUORINE CHEMISTRY, 2000, 102 (1-2) :169-173
[7]   Monofluorination of Organic Compounds: 10 Years of Innovation [J].
Champagne, Pier Alexandre ;
Desroches, Justine ;
Hamel, Jean-Denys ;
Vandamme, Mathilde ;
Paquin, Jean-Francois .
CHEMICAL REVIEWS, 2015, 115 (17) :9073-9174
[8]  
Charushin V. N., 2014, Fluorine in Heterocyclic Chemistry, V2, P111, DOI [10.1007/978-3-319-04435-4_3, 10.1007/978-3-319-04435-4_2]
[9]  
Charushin VN., 2013, FTORKHINOLONY SINTE
[10]   Pure shift NMR approach for fast and accurate extraction of heteronuclear couplings [J].
Chaudhari, Sachin Rama ;
Suryaprakash, N. .
RSC ADVANCES, 2014, 4 (29) :15018-15021