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2,3-Dibromo-2-methyl-5-phenylpentanoic Acid
 
 
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(Z)-2-Bromo-5-phenyl-2-pentene

Division of Organic Chemistry, School of Chemistry F11, The University of Sydney, N.S.W 2006, Australia
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Author to whom correspondence should be addressed.
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Current address: Victorian College of Pharmacy, Monash University (Parkville Campus), 381 Royal Parade, Parkville, Victoria 3052, Australia
Molecules 1998, 3(3), M66; https://doi.org/10.3390/M66
Submission received: 27 February 1998 / Published: 6 March 1998
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 03 m66 i001
The general part of the experimental section [1] has been presented elsewhere. 2,3-Dibromo-2-methyl-5-phenyl-2-pentanoic acid (1.95 g, 5.6 mmol) was refluxed with potassium carbonate (1.93 g, 14.0 mmol) in acetone (50 ml) for 3 hours. The solvent was removed by distillation and the residue was partitioned between ether (100 ml) and water (100 ml). The ether extract was washed with brine (50 ml), dried (Na2SO4), filtered and evaporated under reduced pressure. The crude product was Kugelrohr distilled to yield (Z)-2-bromo-5-phenyl-2-pentene (1.10 g, 88%) as a colourless oil.
B.p. 91°/0.8 mmHg
UV (ethanol) 260 (259), 255 (378) nm.
IR (CDCl3) 3063, 3027(s), 2919(s), 2857, 1644, 1603, 1496(s), 1453, 1427, 1367, 1283, 1167, 1096, 1031, 746, 698 cm-1.
1H-NMR (400 MHz, CDCl3) 2.25 (3H, dt, J 1.4, 1.3 Hz, CH3), 2.45 (2H, m, CH2), 2.69 (2H, bt, J 7.9 Hz, Ph-CH2), 5.62 (1H, tq, J 6.9, 1.4 Hz, =CH), 7.14-7.31 (5H, m, ArH). Stereochemistry confirmed by n.O.e. difference spectroscopy. Irradiation at 5.62 produced a 6% n.O.e. at 2.25 (also 3% at 2.45, 3% at 2.69). Irradiation at 2.25 produced an 2% n.O.e. at 5.62.
13C-NMR (15 MHz, CDCl3) 28.70 (CH3), 33.11, 34.54 (CH2), 123.0 (quat, C2), 125.9 (ArCH), 127.9 (=CH), 128.0 (2xArCH), 141.4 (quat, C1'.
EI-MS 226(M++2, 7%), 224(M+, 7), 146(37), 145(72), 135(26), 133(27), 92(56), 91(100), 77(21), 65(52), 63(22).
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)-2-Bromo-5-phenyl-2-pentene. Molecules 1998, 3, M66. https://doi.org/10.3390/M66

AMA Style

Stoermer MJ, Pinhey JT. (Z)-2-Bromo-5-phenyl-2-pentene. Molecules. 1998; 3(3):M66. https://doi.org/10.3390/M66

Chicago/Turabian Style

Stoermer, Martin J., and John T. Pinhey. 1998. "(Z)-2-Bromo-5-phenyl-2-pentene" Molecules 3, no. 3: M66. https://doi.org/10.3390/M66

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