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

Molecules 1998, 3, M68

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

Martin J. Stoermer^* and John T. Pinhey

Division of Organic Chemistry, School of Chemistry F11, The University of Sydney, N.S.W 2006, Australia.
^* Current address: Victorian College of Pharmacy, Monash University (Parkville Campus), 381 Royal Parade, Parkville, Victoria 3052, Australia. Phone: +61 3 990 39000, Fax: +61 3 99039582, e-mail: martin.stoermer@vcp.monash.edu.au, http://synapse.vcp.monash.edu.au/martin/

Received: 27 February 1998 / Published: 6 March 1998

The general part of the experimental section [1] has been presented elsewhere. The Grignard solution prepared from magnesium turnings (0.27 g, 11 mmol) and (Z)-2-bromo-5-phenyl-2-pentene (2.25 g, 10 mmol) was decanted via double-ended needle from the excess magnesium, and added over 1 hour to a stirred solution of mercuric bromide (3.96 g, 11 mmol) in dry tetrahydrofuran (20 ml). The mixture was refluxed for a further 1 hour and stirred at room temperature overnight. The mixture was centrifuged, the supernatant was decanted, and the precipitate of magnesium bromide was washed with tetrahydrofuran, centrifuged and decanted (3x30 ml cycles). The combined supernatants were evaporated under reduced pressure to yield crude (Z)-5-phenyl-2-penten-2-ylmercury bromide as a grey unstable solid that had to be used within 24 hours of synthesis.

¹H-NMR (90 MHz, CDCl₃) 1.90 (3H, bs, J_199Hg,H 186 Hz, CH₃), 2.10-2.83 (4H, m, 2xCH₂), 6.07 (1H, bt, J 6.87 Hz, J_199Hg,H 561 Hz,=CH), 6.85-7.30 (5H, m, ArH)

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

References and Notes

1. Moloney, M.G.; Pinhey, J.T.; Stoermer, M.J. "Vinyl Cation Formation by Decomposition of Vinyl-lead Triacetates. The reactions of Vinylmercury and Vinyltin Compounds with Lead Tetraacetate." J. Chem. Soc. Perkin Trans. 1 1990, 10, 2645.

Sample Availability: No sample available.