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Org Lett. 2013 Aug 2;15(15):3926-9. doi: 10.1021/ol401670p. Epub 2013 Jul 19.

A fluorine 1,2-migration via aryl cation/radical/radical anion/radical sequence.

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1
Department of Chemistry, University of Pavia, via Taramelli 12, 27100 Pavia, Italy.

Abstract

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.

PMID:
23869692
DOI:
10.1021/ol401670p

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