NUCLEOPHILIC SUBSTITUTION IN THE 10,11-DIHYDRODIBENZ[<i>b,f</i>]IODEPINIUM CATION

Abstract

10,11-Dihydrodibenz[b,f]iodepinium tetrafluoroborate gave only 1-(2-azidophenyl)-2-(2-iodophenylethane with the N₃¯ in aqueous DMSO, while with NO₂¯ it gave 1-(2-nitrophenyl)-2-(2-iodophenyl)ethane (93%), 9,10-dihydrophenanthrene (5%), and traces of phenanthrene. Both in pure and aqueous DMSO this cation with the Br¯ ion was converted into phenanthrene (80% and 68% respectively) and 1-(2-bromophenyl)-2-(2-iodophenyl)ethane (10 and 20%), while in water it gave 9,10-dihydrophenanthrene (75%) and phenanthrene (5%). A new route for the synthesis of 1-(2-aminophenyl)-2-phenylethane starting from this tetrafluoroborate has been proposed.

Authors: T. P. Tolstaya, L. I. Sukhomlinova, A. N. Vanchikov, and N. A. Bumagin.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (1), pp 106-111

http://link.springer.com/article/10.1007/BF02251673