A Fluorine 1,2-Migration via Aryl Cation/Radical/Radical Anion/Radical Sequence

被引：5

作者：

Pretali, Luca ^{[1
]}

Dondi, Daniele ^{[1
]}

D'Angelantonio, Mila ^{[2
]}

Manet, Ilse ^{[2
]}

Fasani, Elisa ^{[1
]}

Monti, Sandra ^{[2
]}

Bovio, Bruna ^{[1
]}

Albini, Angelo ^{[1
]}

机构：

[1] Univ Pavia, Dept Chem, I-27100 Pavia, Italy

[2] CNR, Inst Organ Synth & Photoreact, I-40129 Bologna, Italy

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 15期

关键词：

HALOGEN-DANCE; PHOTOCHEMICAL ISOMERIZATION; REARRANGEMENT; FLUOROQUINOLONES; DERIVATIVES; GENERATION; MIGRATION; CATIONS; CARBON; SHIFTS;

D O I：

10.1021/ol401670p

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Irradiation of a 7-piperazino-8-fluoroquinolone causes formal 1,2-fluorine migration, piperazine loss and reduction, or nucleophile addition in 8. Product study, laser flash photolysis, and computational modeling support F- detachment to yield a triplet 8-quinolyl cation that either inserts intramolecularly or is trapped by Cl-, Br-. However, iodide and pyrrole reduce it to the radical that continues the 'redox tour' (aryl cation -> radical -> radical anion -> radical and then again radical or radical anion) leading to the rearranged products.

引用

页码：3926 / 3929

页数：4

共 50 条

[1] FREE-RADICAL REARRANGEMENT OF A SILYL RADICAL VIA NET 1,2-MIGRATION OF AN ACETOXY GROUP
WILT, JW
KELLER, SM
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1983, 105 (05) : 1395 - 1396
[2] INDO STUDY OF 1,2-FLUORINE ATOM MIGRATION IN 1,1,2,2-TETRA-FLUOROETHYL RADICAL, CATION AND ANION
KOTAKA, M
SATO, S
SHIMOKOSHI, K
[J]. JOURNAL OF FLUORINE CHEMISTRY, 1988, 41 (03) : 371 - 382
[3] THE REGIOCHEMISTRY OF TRAPPED RADICAL ANION-RADICAL CATION PAIRS FROM ARYL SUBSTITUTED PHTHALIMIDES
MAZZOCCHI, PH
KHACHIK, F
[J]. TETRAHEDRON LETTERS, 1981, 22 (42) : 4189 - 4192
[4] POTENTIALITY OF CHLORALKYL RADICAL REARRANGEMENT BY 1,2-MIGRATION OF HYDROGEN-ATOMS IN FREE-RADICAL CHLORINATION AND DEHYDROCHLORINATION PROCESSES
AVERYANOV, VA
[J]. ZHURNAL ORGANICHESKOI KHIMII, 1987, 23 (06): : 1332 - 1334
[5] Allylboronic Esters as Acceptors in Radical Addition, Boron 1,2-Migration, and Trapping Cascades
Jana, Kalipada
Studer, Armido
[J]. ORGANIC LETTERS, 2022, 24 (04) : 1100 - 1104
[6] Three-component 1,2-carboamination of vinyl boronic esters via amidyl radical induced 1,2-migration
You, Cai
Studer, Armido
[J]. CHEMICAL SCIENCE, 2021, 12 (47) : 15765 - 15769
[7] TRIPLET, RADICAL-ANION AND RADICAL CATION SPECTRA OF FUROCOUMARINS
BENSASSON, RV
CHALVET, O
LAND, EJ
RONFARDHARET, JC
[J]. PHOTOCHEMISTRY AND PHOTOBIOLOGY, 1984, 39 (03) : 287 - 291
[8] Transient amino-hydrazino-carbenes:: A radical pathway for intramolecular 1,2-migration reactions
Cattoen, Xavier
Gornitzka, Heinz
Tham, Fook S.
Miqueu, Karinne
Bourissou, Didier
Bertrand, Guy
[J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2007, 2007 (06) : 912 - 917
[9] RADICAL TRANSFORMATIONS OF NUCLEOSIDES WITH (ME(3)SI)(3)SIH - GENERATION OF A C-1' RADICAL THROUGH 1,2-MIGRATION OF AN ACYLOXY GROUP
GIMISIS, T
IALONGO, G
ZAMBONI, M
CHATGILIALOGLU, C
[J]. TETRAHEDRON LETTERS, 1995, 36 (37) : 6781 - 6784
[10] 1,2-MIGRATION OF FLUORINE ATOM IN CH2FCF2 RADICAL PRODUCED BY THE ADDITION OF A HYDROGEN-ATOM TO TRIFLUOROETHYLENE
KOHIDA, T
KOTAKA, M
SATO, S
ISHIDA, T
YAMAMOTO, K
YAMAZAKI, T
KITAZUME, T
[J]. BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (09) : 3131 - 3135

← 1 2 3 4 5 →