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Nucleophilic substitution in the 10,11-dihydrodibenz[b,f]iodepinium cation

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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Authors
  1. T. P. Tolstaya
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  2. L. I. Sukhomlinova
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  3. A. N. Vanchikov
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  4. N. A. Bumagin
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Additional information

M. V. Lomonosov Moscow State University, Moscow 119899, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, 110–115, January, 1999.

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Tolstaya, T.P., Sukhomlinova, L.I., Vanchikov, A.N. et al. Nucleophilic substitution in the 10,11-dihydrodibenz[b,f]iodepinium cation. Chem Heterocycl Compd 35, 106–111 (1999). https://doi.org/10.1007/BF02251673

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