[CH:1]([S:3]([C:6]1[CH:11]=[CH:10][C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][CH:7]=1)(=[O:5])=[O:4])=[CH2:2].[CH3:16][SnH:17]([CH3:19])[CH3:18]>[Hg].C1(C)C=CC=CC=1>[C:12]([C:9]1[CH:10]=[CH:11][C:6]([S:3]([CH2:1][CH2:2][Sn:17]([CH3:19])([CH3:18])[CH3:16])(=[O:5])=[O:4])=[CH:7][CH:8]=1)([CH3:15])([CH3:14])[CH3:13]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 9.5 g (42.5 mmoles) of 4-t-butylphenyl vinyl sulfone, 7.0 g (42.5 mmoles) of trimethyltin hydride and 10 ml. of toluene, stoppered, and placed in a 20°C water bath. The tube was irradiated for 35 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. Solvent was stripped off at reduced pressure on a rotary evaporator. Recrystallization of the solid product from cyclohexane gave 11.4 g of 2-(4-t-butylphenylsulfonyl)ethyltrimethylstannane, m.p. 118°-120°C. The presence of both the sulfonyl and trimethyltin groups was indicated by the strong infrared absorption bands at 1310 cm-1, 1262 cm-1, 1145 cm-1 (--SO2 --) and 770 cm-1 ((CH3)3Sn) using a KBr disc. Nuclear magnetic resonance spectroscopy (NMR) showed the following:
Wird geladen…
