Lithium diisopropylamide → HCID 85749769, compound

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Reaction Steps

A solution of 1,1-dibutyl-1-stannacyclohexadienyllithium prepared from 1,1-dibutyl-1-stannacyclohexa-2,5-diene (0.08 g, 2.67 mmol) and 2.67 mmol of lithium diisopropylamide (LDA) in 20 mL of THF was added to a solution of 1,1-dibutyl-4-(2-bromoethyl)-1-stannacyclohexa-2,5-diene (1.0 g, 2.46 mmol) in 5 mL THF at −78° C. After stirring approximately 16 hours, 10 mL of water were added and the product was extracted with pentane, dried over MgSO4, and evaporated to dryness. The red residue left contained 1.25 g (81 percent) of crude product. 1H NMR (C6D6): δ 0.9-1.5 (m, Bu), 1.62 (m,—CH2CH2), 3.11 (m, Hγ), 6.26 (dd, J=14.2, 1.5), 6.61 (dd, J=14.2, 4.3); 13C NMR (C6D6): δ 151.0 (Cβ), 126.4 (Cα), 45.1 (Cγ), 33.7 (CH2CH2), 30.0, 27.8, 14.4, 11.4 (Bu); HRMS (El): calculated for C24H41 120Sn2 (M—Bu): 569.1252, found 569.1237.

Provenance & Evidence