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Synthesis and structure of bromonitro-6(5H)-phenanthridinones
Authors:A M Andrievskii  O V Chelysheva  A N Poplavskii  V V Nikonov  L A Chetkina  V K Bel'skii  V E Zavodnik  A A Perov  N A Andronova  K M Dyumaev
Institution:(1) Research Institute for Organic Intermediates and Dyes, 103787 Moscow;(2) L. Ya. Karpov Research Institute for Physical Chemistry, 103064 Moscow
Abstract:Treatment of 2-bromo-6(5H)-phenanthridone with nitrating mixture or fuming nitric acid results in nitration, debromination, and bromination in the 10-position. The brominating agent is apparently Br+, formed in the reaction mixture following replacement of the bromine in the 2-position by a nitro-group. Monocrystals of 2-bromo-1,4,8-trinitro-6(5H)-phenanthridinone and 10-bromo-2,4,8-trinitro-6(5H)-phenanthridinone have been subjected to x-ray diffraction examination. PMR has been used for structural identification.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 789–795, June, 1990.We thank A. N. Sobolev for assistance in calculating the structure of (III).
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