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Über Die SiN-bindung: XLIV. Die Umsetzung Von Benzophenon Mit Bis- Und Tris(trimethylsilyl)amin☆

K. Ruehlmann, H. Schilling, H. Frey
Published 1985 · Chemistry

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1,1,3-Triphenyl-1H-isoindole (I) is obtained in yields up to 66% by reacting benzophenone with tris(trimethylsilyl)amine or with bis(trimethylsilyl)amine and chlorotrimethylsilane in the presence of catalytic amounts of a Lewis acid at 230–280°C in a sealed tube or with equimolar amounts of a Lewis acid at 210°C without using a sealed tube. At temperatures above 280°C the same reactions yield mixtures of I with 1,2,3-triphenyl-2H-isoindole (II), whose fraction can reach 25% of the isoindole mixture. Mechanistic investigations on the new isoindole synthesis indicated, that azaallenium cations are involved as intermediates.
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