Tributylstannane → trans-1-Tributylstannyl-3-trimethylsilyloxy-1-octene

Participants

Reaction Steps

Under an argon atmosphere, 3-trimethylsilyloxy-1-octyne (47, 2.00 g, 10.08 mmol) and tributyltin hydride (2.70 mL, 10.18 mmol) were irradiated with a 275 W GE sunlamp, without solvent, for 4 h to produce 49: 1H NMR (CDCl3) δ 6.04 (d, J=18.9 Hz, 1H), 5.93 (dd, J1 =18.9 Hz, J2 =5.4 Hz, 1H), 4.04 (q, J1 =6.5 Hz, J2 =5.6 Hz, 1H), 1.52, 1.34 (2m, 26H), 0.91 (m, 12H), 0.11 (s, 9H). 1H NMR analysis revealed that 49 was only ca. 85% pure. Other isomers, presumed to be the cis-vinyl-stannane and the regioisomeric vinylstannane, could be clearly seen in the vinyl region of the NMR spectrum. The production of these impurities in this reaction has been previously described.

Provenance & Evidence