Premium
Neue Äthylenimin‐Derivate in der Chinonreihe
Author(s) -
Marxer A.
Publication year - 1957
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19570400232
Subject(s) - chemistry , halogen , bromine , benzoquinone , medicinal chemistry , 1,4 benzoquinone , quinone , alkoxy group , stereochemistry , organic chemistry , alkyl
2,6‐Dimethoxy‐benzoquinone (11) does not react with amines, such as ethylenimine, at room temperature nor at slightly elevated temperatures contrary to 2,5‐dimethoxy‐benzoquinone. In the 3,5‐dibromo‐2,6‐dimethoxy‐benzoquinone (VI), however, the same, previously unreactive methoxy groups are exchanged by amines. The two remaining bromine atoms can then be replaced by alkoxy or thioalkoxy groups (type IX). Reasons for this behaviour are discussed. The two halogen atoms in 2,5‐Diamino‐3,6‐dichloro‐benzoquinone are rather unreactive towards further treatment with amines. In 2,5‐bis‐acylamino‐3,6‐dichloro‐benzoquinones the halogen groups are highly reactive, so that they are exchanged by ethylenimine t o give compounds of type XVI.