Recent Advances in Organic Chemistry

Cover Recent Advances in Organic Chemistry
Recent Advances in Organic Chemistry
Alfred W Alfred Walter Stewart
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Bamberger 1 has found that when quinoles such as those shown below are subjected to the action of hydrogen, or, better, hydroxyl ions, they are converted into homologues of hydro- quinone, as the f ormulae indicate : HO CH 3 X HO CH II II * HO C. CH 3 O In these cases, it is clear that the forces which bring about the intramolecular change are of a strength sufficient to elimi- nate a hydrogen atom from the nucleus and to replace it by a methyl radicle. A much more powerful action is shown in a
...nother case, which was investigated by Zincke. 2 If we treat tetrabromo-ethyl-quinole with concentrated sulphuric acid in the cold, we find that hydrobromic acid is eliminated, and the ethyl radicle replaces the bromine atom which has been driven out of the nucleus : 1 Bamberger, Ber. , 1900, 33, 3618. 2 Zincke, Sir. , 1901, 34, 253.
THE QUINOLES 217 HO C 2 H 5 X ;; ' A- "'' Br. G C. Br -HBr Br. C C . C 2 H 5 II II > II II Br. C C. Br Br. C C. Br v v II II O A still more extraordinary wandering is seen in a case mentioned by Auwers.


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