Three-step regioselective synthesis of 2,3-difluorohalobenzenes using tetrafluoroethylene and buta-1,3-diene as starting building blocks

被引：4

作者：

Volchkov, N. V. ^{[1
]}

Lipkind, M. B. ^{[1
]}

Nefedov, O. M. ^{[1
]}

Egorov, M. P. ^{[1
]}

机构：

[1] Russian Acad Sci, ND Zelinsky Inst Organ Chem, 47 Leninsky Prosp, Moscow 119991, Russia

来源：

RUSSIAN CHEMICAL BULLETIN | 2021年 / 70卷 / 05期

关键词：

tetrafluoroethylene; buta-1; 3-diene; cycloaddition; tetrafluorocyclohexenes; halogenation; dihalotetrafluorocyclohexanes; dehydrohalogenation; 1-bromo-2; 3-difluorobenzene; 1-chloro-2; 1-halo-5; 5; 6; 6-tetrafluorocyclohexenes; 2+2 CYCLOADDUCTS; FLUORINE; CYCLOPENTADIENE; AROMATIZATION; DERIVATIVES; GENERATION; BUTADIENES; CHEMISTRY;

D O I：

10.1007/s11172-021-3168-5

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The gas-phase copyrolysis of tetrafluoroethylene and buta-1,3-diene in a flow tube reactor at 490-510 degrees 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.

引用

页码：925 / 932

页数：8

共 43 条

[21] Facile synthesis of the DD3R zeolite: performance in the adsorptive separation of buta-1,3-diene and but-2-ene isomers
Gucuyener, Canan
van den Bergh, Johan
Joaristi, Alberto Martinez
Magusin, Pieter C. M. M.
Hensen, Emiel J. M.
Gascon, Jorge
Kapteijn, Freek
JOURNAL OF MATERIALS CHEMISTRY, 2011, 21 (45) : 18386 - 18397
[22] SUBSTITUENT EFFECTS ON FORMATION AND BOND PROPERTIES OF TRICARBONYL(BUTA-1,3-DIENE)IRON, TRICARBONYL(TRANS-1-CHLOROBUTA-1,3-DIENE)IRON AND EXPERIMENTS ON SYNTHESIS OF TRICARBONYL(TRANS,TRANS 1,2,3,4-TETRACHLOROBUTA-1,3-DIENE)IRON
BRUNE, HA
SCHWAB, W
HORLBECK, G
TETRAHEDRON, 1972, 28 (16) : 4455 - &
[23] Extraction and Coordination Properties of 2,3-Bis(diphenylphosphinyl)buta-1,3-diene and 3,4-Bis(diphenylphosphinyl)-2,5-dimethylhexa-2,4-diene
Brel, V. K.
Artyushin, O. I.
Morgalyuk, V. P.
Vologzhanina, A. V.
Turanov, A. N.
Karandashev, V. K.
RUSSIAN JOURNAL OF COORDINATION CHEMISTRY, 2022, 48 (04) : 201 - 209
[24] Extraction and Coordination Properties of 2,3-Bis(diphenylphosphinyl)buta-1,3-diene and 3,4-Bis(diphenylphosphinyl)-2,5-dimethylhexa-2,4-diene
V. K. Brel
O. I. Artyushin
V. P. Morgalyuk
A. V. Vologzhanina
A. N. Turanov
V. K. Karandashev
Russian Journal of Coordination Chemistry, 2022, 48 : 201 - 209
[25] Photochemical Synthesis of cis,trans,cis-1,2,3,4-Tetrakis(diphenylphosphanyl)buta-1,3-diene and Its Metal Coordination
Oberhauser, Werner (werner.oberhauser@iccom.cnr.it), 2018, Wiley-VCH Verlag (2018)
[26] Competition between hetero-Diels-Alder and cheletropic additions of sulfur dioxide to 2-substituted buta-1,3-dienes.: Synthesis of 2-(1-naphthyl)and 2-(2-naphthyl)buta-1,3-diene
Roversi, E
Vogel, P
HELVETICA CHIMICA ACTA, 2002, 85 (03) : 761 - 771
[27] Photochemical Synthesis of cis,trans,cis-1,2,3,4-Tetrakis(diphenylphosphanyl)buta-1,3-diene and Its Metal Coordination
Prock, Johannes
Ehrmann, Katharina
Viertl, Wolfgang
Pehn, Richard
Pann, Johann
Roithmeyer, Helena
Bendig, Marvin
Villalon, Alba Rodriguez
Kopacka, Holger
Dumfort, Alexander
Oberhauser, Werner
Clausing, Simon T.
Knoer, Guenther
Brueggeller, Peter
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY, 2018, (46) : 4962 - 4971
[28] SUBSTITUENT EFFECTS IN BUTA-1,3-DIENE PHOTOCHEMISTRY - A CAS-SCF STUDY OF 2,3-DIMETHYLBUTADIENE AND 2-CYANOBUTADIENE EXCITED-STATE REACTION PATHS
OLIVUCCI, M
BERNARDI, F
OTTANI, S
ROBB, MA
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1994, 116 (05) : 2034 - 2048
[29] Synthesis of 2-(buta-1,3-diynyl)-N,N-dimethylanilines using reductive methylation step
Kulyashova, Alexandra E.
Mikheeva, Elena V.
Danilkina, Natalia A.
Balova, Irina A.
MENDELEEV COMMUNICATIONS, 2014, 24 (02) : 102 - 104
[30] SYNTHESIS AND STRUCTURE OF 2,3-BIS(5-TERT-BUTYL-2-METHOXYPHENYL)BUTA-1,3-DIENE BY BROMINE ELIMINATION OF (Z)-1,4-DIBROMO-2,3-BIS(5-TERT-BUTYL-2-METHOXYPHENYL)-2-BUTENE
Tazoe, Kazuya
Uchikawa, Yuki
Feng, Xing
Yamato, Takehiko
SYNTHETIC COMMUNICATIONS, 2012, 42 (21) : 3128 - 3139

← 1 2 3 4 5 →