Trimethylstannane → 4-(4-t-Butylphenylsulfonyl)butyltrimethylstannane

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Reaction Steps

An 80 ml, two-necked, pyrex glass Schlenk reaction tube containing a Teflon coated magnetic stir bar was swept thoroughly with nitrogen and maintained in an air-free condition. The tube was charged with 10.7 g (42.5 mmoles) of 3-butenyl-4-t-butylphenyl sulfone and 7.0 g (42.5 mmoles) of trimethyltin hydride, stoppered, and placed in a 20° C. water bath. The tube was irradiated for 70 hours by a 100 watt mercury vapor lamp which was situated in a large test tube and placed in the same bath 5-10 cm. from the reaction tube. Recrystallization of the solid product from petroleum ether afforded 3.6 g of 4-(4-t-butylphenylsulfonyl)butyltrimethylstannane, m.p. 80°-81.8° C. The presence of both the sulfonyl and trimethyltin moieties was indicated by strong infrared absorption bands at 1300 cm-1, 1282 cm-1, 1147 cm-1 (--SO2 --) and 780 cm-1 [(CH3)3Sn--] employing a KBR disc. Nuclear magnetic resonance spectroscopy (NMR) showed the following:

Provenance & Evidence