Zur Reaktion von Halogen(trimethylsilyl)benzolen mit Elektrophilen und Basen : Carbodesilylierung und Eliminierung als Konkurrenzreaktionen

Abstract

Elimination to dehydrobenzenes takes place as competitive reaction in the base-catalyzed carbodesilylation of 1-halo-2-(trimethylsilyl)benzenes 1 with carbonyl compounds 2 in the presence of furans 3, 6. Elimination is preferred with increasing leaving tendency of the halides (I > Br > > Cl > > F) and with decreasing reactivity of the carbonyl compounds. Exclusive elimination to 1,2-didehydrobenzenes - which are trapped with furans - occurs in the reaction when no electrophiles are present.