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Tributyl-[(Z)-5-phenyl-2-penten-2-yl]stannane

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), M67; https://doi.org/10.3390/M67
Submission received: 27 February 1998 / Published: 6 March 1998
(This article belongs to the Section Molbank Section of Molecules, 1997-2001)
Molecules 03 m67 i001
The general part of the experimental section [1] has been presented elsewhere. The Grignard solution prepared from magnesium turnings (0.11 g, 4.4 mmol) and (Z)-2-bromo-5-phenyl-2-pentene (0.90 g, 4 mmol) in dry tetrahydrofuran (15 ml) was decanted via double-ended needle from the excess magnesium, and titrated with tributyltin chloride until the solution decolourised. The resulting solution was stirred at room temperature for 1 hour and the solvent was removed under reduced pressure. The residue was partitioned between ether (30 ml) and water (30 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 tributyl-[(Z)-5-phenyl-2-penten-2-yl]stannane (1.13 g, 59%) as a colourless oil.
B.p. 180°/0.03 mmHg
IR (CDCl3) 2958(s), 2927(s), 2872, 2858, 1454, 1414, 1377, 1078, 698 cm-1.
1H-NMR (400 MHz, CDCl3) 0.82-0.96 (15H, m, 3xCH2 and 3xCH3), 1.31 (6H, m, 3xCH2), 1.47 (6H, m, 3xCH2), 1.89 (3H, dt, J 1.7, 1.2 Hz, J119Sn,H and J117Sn,H give average of 43 Hz, CH3), 2.28 (2H, m, CH2), 2.65 (2H, bt, J 7.8 Hz, Ph-CH2), 6.09 (1H, tq, J 7.2, 1.7 Hz, J119Sn,H and J117Sn,H give average of 133 Hz, =CH), 7.16-7.33 (5H, m, ArH). Stereochemistry confirmed by n.O.e. difference spectroscopy. Irradiation at 1.89 produced a 3% n.O.e. at 6.09 . Irradiation at 6.09 produced an 9% n.O.e. at 1.89 (also 5% at 2.28, 4% at 2.65).
13C-NMR (100 MHz, CDCl3) 10.05 (CH3), 13.83 (CH2), 27.52 (CH3), 27.52 (CH2), 29.34, 36.79, 37.00 (CH2), 125.6, 128.2, 128.3 (ArCH), 138.7 (quat, C2), 139.7 (=CH),, 141.9 (quat, C1').
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. Tributyl-[(Z)-5-phenyl-2-penten-2-yl]stannane. Molecules 1998, 3, M67. https://doi.org/10.3390/M67

AMA Style

Stoermer MJ, Pinhey JT. Tributyl-[(Z)-5-phenyl-2-penten-2-yl]stannane. Molecules. 1998; 3(3):M67. https://doi.org/10.3390/M67

Chicago/Turabian Style

Stoermer, Martin J., and John T. Pinhey. 1998. "Tributyl-[(Z)-5-phenyl-2-penten-2-yl]stannane" Molecules 3, no. 3: M67. https://doi.org/10.3390/M67

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