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Short Note

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

by
Martin J. Stoermer
* and
John T. Pinhey
Division of Organic Chemistry, School of Chemistry F11, The University of Sydney, N.S.W 2006, Australia
*
Author to whom correspondence should be addressed.
*
Current address: Victorian College of Pharmacy, Monash University (Parkville Campus), 381 Royal Parade, Parkville, Victoria 3052, Australia
Molecules 1998, 3(3), M69; https://doi.org/10.3390/M69
Submission received: 27 February 1998 / Published: 6 March 1998
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Versions Notes
Molecules 03 m69 i001
The general part of the experimental section [1] has been presented elsewhere. To a stirred solution of (Z)-5-phenyl-2-penten-2-ylmercury bromide (3 mmol) in dry tetrahydrofuran (40 ml) was added silver acetate (3 mmol) and the mixture was stirred at room temperature in the dark for 16 hours, filtered through Celite(TM) and the solvent was removed. The crude product was recrystallised from cyclohexane/light petroleum to yield (Z)-5-phenyl-2-penten-2-ylmercury acetate (78%) as colourless plates.
M.p. 85°
Anal. calc. for C13H16HgO2 (404.85): C 38.6, H 4.0; found: C 38.9, H 4.1.
UV (ethanol) 217sh (4180) nm.
IR (film) 2941, 1628(s), 1605(s, C=O), 1368(s),1317(s) cm-1.
1H-NMR (400 MHz, CDCl3) 1.94 (3H, bs, J199Hg,H 191 Hz, CH3), 2.04 (3H, s, OCO2CH3), 2.46 (2H, dt, J 7.3, 7.1 Hz, CH2), 2.71 (2H, bt, J 7.1 Hz, Ph-CH2), 6.01 (1H, tq, J 7.3, 1.7 Hz, J199Hg,H 549 Hz, =CH), 7.13-7.31 (5H, m, ArH).
13C-NMR (15 MHz, CDCl3) 23.38, 26.49 (CH3), 35.91, 37.92 (CH2), 126.0, 128.4, 128.8 (ArCH), 136.7 (=CH), 141.0 (quat), 142.7 (quat), 177.3 (C=O).
EI-MS 406(M+, <1%), 347(M+-OAc, <1%), 146(16), 145(86), 144(56), 129(43), 117(20), 104(33), 92(15), 91(100), 77(10), 65(19).
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. [Google Scholar] [CrossRef]
Sample Availability: No sample available.

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MDPI and ACS Style

Stoermer, M.J.; Pinhey, J.T. [(Z)-5-Phenyl-2-penten-2-yl]mercury Acetate. Molecules 1998, 3, M69. https://doi.org/10.3390/M69

AMA Style

Stoermer MJ, Pinhey JT. [(Z)-5-Phenyl-2-penten-2-yl]mercury Acetate. Molecules. 1998; 3(3):M69. https://doi.org/10.3390/M69

Chicago/Turabian Style

Stoermer, Martin J., and John T. Pinhey. 1998. "[(Z)-5-Phenyl-2-penten-2-yl]mercury Acetate" Molecules 3, no. 3: M69. https://doi.org/10.3390/M69

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