A stable enol from a 6-substituted benzanthrone and its unexpected behaviour under acidic conditions.
Treatment of benzanthrone (1) with biphenyl-2-yl lithium leads to the surprisingly stable enol 4, which is converted by dehydrogenation into the benzanthrone derivative 7. Under acidic conditions 4 isomerises to the spiro compound 11 and the bicyclo[4.3.1]decane derivative 12. Furthermore, the formation of 7 and the hydrogenated compound 13 is observed. A mechanism for the formation of the reaction products is proposed and supported by DFT calculations.
Debeaux
Marc
M
Labor für Elektrooptik am Institut für Hochfrequenztechnik, Technische Universität Braunschweig, Bienroder Weg 94, 38106 Braunschweig, Germany.
Brandhorst
Kai
K
Jones
Peter G
PG
Hopf
Henning
H
Grunenberg
Jörg
J
Kowalsky
Wolfgang
W
Johannes
Hans-Hermann
HH