Abstract
The synthesis of 1-(tri- n-butylstannyl)indene, 1, was carried out by the reacting lithium indenide with tributylstannyl chloride. The pale yellow product was collected by distillation in 65% yield, and the procedure is scalable to large quantities. Examination of the room-temperature 1H NMR spectrum of 1 revealed a fluxional process in which the tributylstannyl group was rapidly interchanging between the 1 and 3 positions on indene. A variable-temperature 1H NMR study was performed on 1 from −60°C to +40°C and the free energy of activation for the 1,3-interchange was calculated as 15.4 kcal mol −1 at 60°C, using the Eyring equation. This result is compared to previous studies of the 1,3 migrations of trimethylsilyl and trimethylstannyl groups on indene.
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