No abstract

We have now been able to show that a nucleophilic addition takes place on reaction of triphenylstannyllithium with carbon disulfide. The initial product (1) can be trapped by alkylation with methyl or ethyl iodide in tetrahydrofuran (THE').

ORGANOLITHIUM COMPOUNDS OF GROUP IV AND V ELEMENTS 619 119 g. (5.2 moles) of sodium dispersed in 5 1. of refined tetrahydrofuran. The reaction temperature was maintained at 0 to 5°d uring the addition and for 1 hr. thereafter. After further stirring at room temperature for 7 hr., the solution was cooled to 0°and 2.5 moles of freshly prepared iron(II) chloride14 in 2 1. of refined tetrahydrofuran was added in portions with vigorous stirring. The temperature rose to 18°d uring this addition. The resulting suspension was stirred at ambient temperature for 1 hr., then at 55 to 60°f or 12 hr. The solvent was then distilled at reduced pressure, and 5 1. of low boiling petroleum ether was added. The resulting solids were removed by centrifugation, and the petroleum ether and residual tetrahydrofuran were distilled to a flask temperature of 100°/10 mm. The residual concentrate was refined on a DPI molecular still to yield 1684 g.(1.34 moles, 53.5%) of an oil, vapor temperature 290- (14) Prepared by the method of G. Wilkinson, Org. Syntheses, 36, 31 (1956), using a 40 mole per cent excess of iron powder. 295°/0.004 mm. Fourteen separate fractions were collected nsD°1 .4916 to 1.4931; the spectra of all 14 fractions were practically identical. Composite, re°D°1 .4922.An infrared spectrum of this material indicated that it was free of Si-H and Si-0-Si bonds. There were weak bonds at 9 and 9.95 µ. These bonds also appeared in the spectrum of chlorotri-n-dodecylsilane.