113600-22-9Relevant articles and documents
Synthesis of Fluorinated Derivatives of Benzofluoranthene and Indenopyrene and 8,9-dihydro-8,9-epoxybenzofluoranthene
Rice, Joseph E.,Czech, Anna,Hussain, Nalband,LaVoie, Edmond J.
, p. 1775 - 1779 (2007/10/02)
The synthesis of several select fluorinated derivatives of benzofluoranthene and indenopyrene is described.In the benzofluoranthene series, the 8- and 9-fluoro derivatives have been prepared by Wittig reaction of the 1,2-bis salt of the appropriate fluorobenzene with acenaphthenequinone under phase-transfer conditions.The synthesis of 2-fluoroindenopyrene was achieved by photocyclization of 1-(β,β-difluorovinyl)benzofluoranthene followed by dehydrofluorination in methanolic sodium methoxide.This represents a new method for the construction of the indenopyrene skeleton. 8,9-Difluoroindenopyrene was prepared from 1-(2-amino-4,5-diflurophenyl)pyrene by diazotization followed by coupling in the presence of copper-bronze.In addition to these fluorinated derivatives, the synthesis of 8,9-dihydro-8,9-epoxybenzofluoranthene, a suspect ultimate tumorigenic metabolite of benzofluoranthene, is reported.This arene oxide was prepared from the trans-8,9-bromo acetate by benzylic bromination and subsequent treatment with sodium methoxide in anhydrous THF.
