bis-[(Z)-5-Phenyl-2-penten-2-yl]mercury

The general part of the experimental section [1] has been presented elsewhere. To a stirred solution of sodium hydroxide (20 eq.) in distilled water (4 ml) was addded stannous chloride (1.5 eq.) in distilled water (10 ml), A suspension of (Z)-5-Phenyl-2-penten-2-ylmercury bromide (2 mmol) in water (10 ml) and ethanol (10 ml) was then added over 1 hour, and the mixture was stirred at room temperature overnight, diluted with water (50 ml) and extracted with ether (3x40 ml). The combined ether extracts were dried (Na₂SO₄), filtered and evaporated under reduced pressure. Kugelrohr distillation gave the title compound in 85% yield.

B.p. 200°/0.1 mmHg.

UV (ethanol) 272(sh) (1234), 264sh (1728), 237sh (5266) nm.

IR (film) 3026, 2928, 2902(s), 2841, 1602(s), 1496, 1453(s), 842, 747(s), 698(s) cm^-1.

¹H-NMR (90 MHz, CDCl₃) 1.83 (3H, bs, J_199Hg,H 87 Hz, CH₃), 2.10-2.88 (4H, m, 2xCH₂), 6.51 (1H, bt, J 6.6 Hz, =CH), 6.82-7.42 (5H, m, ArH).

EI-MS 146(28%), 145(87), 144(51), 129(27), 117(22), 104(10), 92(18), 91(100), 77(10), 65(18).

Acknowledgment: The authors gratefully acknowledge financial support from the Australian Research Council and The University of Sydney.