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

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