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The Meisenheimer Reaction of 1,4,5,8‐Tetraazaphenanthrene and Benzo [f] Quinoxaline N‐Oxides

par Hinkens, Raymonde ;Faucon, F.;Owen, J.P.
Référence Bulletin des Sociétés chimiques belges, 93, 11, page (953-960)
Publication Publié, 1984

Article révisé par les pairs

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Résumé :

1,4,5,8‐Tetraazaphenanthrene‐N1‐oxide (II) reacts with POCl3 to give equivalent amounts of 2‐chloro‐tetraazaphenanthrene (V) and 9‐chloro‐tetraazaphenanthrene (VI). Benzo [f] quinoxaline‐N1‐oxide (IV) gives with the same reagent 2‐chloro‐benzo [f] quinoxaline (IX, 57%) and 9‐chloro‐benzo[f]quinoxaline (X, 15%). This last result suggests that the chloride ion has entered position 9− of II rather than position 10−, in agreement with electronic effects. Copyright © 1984 Wiley‐VCH Verlag GmbH & Co. KGaA, Weinheim