1,1',1''-(Chlorosilylidyne)tris(benzene) → (4-Triphenylsilyloxyimino-cyclohexa-2,5-dienylidene)-phenyl-acetonitrile

Participants

Reaction Conditions

Reaction Steps

7 g (31 mmol) of (4-Hydroxyimino-cyclohexa-2,5-dienylidene)-phenyl-acetonitrile, prepared as described in example 1.1, are dissolved in 80 ml of THF and cooled in an ice bath. After adding 10 g (34 mmol) of triphenylchlorosilane to the solution, 4.7 g (47 mmol) of triethylamine are added dropwise, keeping the temperature below 5° C. While the reaction mixture is stirred at 5° C. for 90 min, a precipitate is formed. The precipitate is filtered off and washed with THF. The filtrate is concentrated by a rotary evaporator to afford a red liquid. The residue is diluted with 2-PrOH and stirred at room temperature for 30 min. After cooling the mixture in an ice bath, the solid is isolated by filtration and washed with 2-PrOH. The product is obtained in the form of a pale yellow solid, mp 161-165° C. (Dec). The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ [ppm]: 6.79(Z)/6.94(E) (dd, 1H), 7.04(Z)/7.15(E) (dd, 1H), 7.32-7.71 (m, 22H). 1H-NMR reveals that the product is a 77:23 mixture of Z and E isomers. The signals are tentatively assigned to Z and E isomers.

Provenance & Evidence